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1485-00-3

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1485-00-3 Usage

Description

3,4-Methylenedioxy-beta-nitrostyrene (MDBN), also known as 1485-00-3, is a cell permeable, irreversible inhibitor of p97 with an IC50 of less than 10 μM. It is characterized by its yellow powder form and is known for its ability to inhibit Src and Syk kinases, preventing the phosphorylation and cytoskeletal association of GPIIb/IIIa and talin.

Uses

Used in Pharmaceutical Industry:
3,4-Methylenedioxy-beta-nitrostyrene is used as a pharmaceutical compound for its inhibitory effects on p97, Src, and Syk kinases. Its application is particularly relevant in the development of treatments targeting various diseases and conditions where these kinases play a significant role in their progression.
Used in Research Applications:
MDBN is utilized as a research tool in the field of cell biology and molecular biology. It aids in understanding the roles and interactions of p97, Src, and Syk kinases in cellular processes and signaling pathways, contributing to the advancement of scientific knowledge in these areas.
Used in Drug Development:
3,4-Methylenedioxy-beta-nitrostyrene serves as a starting point for the development of new drugs targeting kinases involved in various diseases. Its irreversible inhibition properties make it a valuable compound in the design and synthesis of potential therapeutic agents.
Used in Diagnostic Applications:
MDBN can be employed in the development of diagnostic tools and assays to detect and monitor the activity of p97, Src, and Syk kinases. This can be particularly useful in the early detection and monitoring of diseases associated with the dysregulation of these kinases.

Biological Activity

Selective inhibitor of Src and Syk tyrosine kinases. Displays antiaggregative activity via inhibition of GPIIb/IIIa activation (IC 50 = 12.7 μ M for thrombin-induced platelet aggregation). Exhibits no effects on Ca 2+ -dependent enzymes, PKC or arachidonic acid metabolism.

References

1) Chou et al. (2011), Quantitative cell-based protein degradation assays to identify and classify drugs that target the ubiquitin-proteasome system; J. Biol. Chem., 286 16546

Check Digit Verification of cas no

The CAS Registry Mumber 1485-00-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,8 and 5 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1485-00:
(6*1)+(5*4)+(4*8)+(3*5)+(2*0)+(1*0)=73
73 % 10 = 3
So 1485-00-3 is a valid CAS Registry Number.
InChI:InChI=1/C9H7NO4/c11-10(12)4-3-7-1-2-8-9(5-7)14-6-13-8/h1-5H,6H2/b4-3-

1485-00-3 Well-known Company Product Price

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  • Alfa Aesar

  • (L09139)  3,4-Methylenedioxy-beta-nitrostyrene, 98%   

  • 1485-00-3

  • 10g

  • 1064.0CNY

  • Detail
  • Alfa Aesar

  • (L09139)  3,4-Methylenedioxy-beta-nitrostyrene, 98%   

  • 1485-00-3

  • 50g

  • 4074.0CNY

  • Detail

1485-00-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,4-Methylenedioxy-beta-nitrostyrene

1.2 Other means of identification

Product number -
Other names 5-(2-Nitrovinyl)benzo[d][1,3]dioxole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1485-00-3 SDS

1485-00-3Synthetic route

piperonal
120-57-0

piperonal

nitromethane
75-52-5

nitromethane

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

Conditions
ConditionsYield
With sodium acetate; methylamine In methanol; ethanol for 2h; Henry Nitro Aldol Condensation;91%
With aluminum oxide; potassium carbonate for 0.0666667h; microwave irradiation;90%
With ethylenediamine functionalized magnetic Fe3O4 supported on SiO2 nanoparticles; air at 80℃; for 4h;89%
1,3-benzodioxol-5-ylmethyl amine
2620-50-0

1,3-benzodioxol-5-ylmethyl amine

nitromethane
75-52-5

nitromethane

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

Conditions
ConditionsYield
With 4-(4-fluorophenyl)naphthalene-1,2-dione; oxygen at 80℃; for 12h;53%
sodium compound of nitromethyl-<3.4-methylenedioxy-phenyl>-carbinol

sodium compound of nitromethyl-<3.4-methylenedioxy-phenyl>-carbinol

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

Conditions
ConditionsYield
With acetic acid; zinc(II) chloride
benzene-1,2-diol
120-80-9

benzene-1,2-diol

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / dimethyl sulfoxide / 95 - 120 °C
2: trichlorophosphate
3: sodium acetate; methylamine / ethanol; methanol / 2 h
View Scheme
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trichlorophosphate
2: sodium acetate; methylamine / ethanol; methanol / 2 h
View Scheme
piperonal
120-57-0

piperonal

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

Conditions
ConditionsYield
With ammonium acetate; acetic acid at 100℃;
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

3,4-methylenedioxyphenylethylamine
1484-85-1

3,4-methylenedioxyphenylethylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 70℃; for 4h;100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 4h;95%
With diisobutylaluminium hydride In 1,4-dioxane at 60℃; for 3h;82%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

cyclohexanone
108-94-1

cyclohexanone

(S)-2-((R)-1-(benzo[d][1,3]dioxol-6-yl)-2-nitroethyl)cyclohexanone

(S)-2-((R)-1-(benzo[d][1,3]dioxol-6-yl)-2-nitroethyl)cyclohexanone

Conditions
ConditionsYield
Stage #1: cyclohexanone With (S)-1-(2,3,4,6-tetra-O-acetyl)glucosyl-3-(pyrrolidin-2-ylmethyl)-thiourea trifluoroacetate; triethylamine at 20℃; for 0.333333h;
Stage #2: 5-(2-nitrovinyl)benzo[1,3]dioxole With butyric acid at -15℃; for 52h; Michael condensation;
99%
Stage #1: cyclohexanone With C2HF3O2*C17H19N2O2PS; triethylamine at 25℃; for 0.5h;
Stage #2: With benzoic acid for 0.25h;
Stage #3: 5-(2-nitrovinyl)benzo[1,3]dioxole at -30℃; for 40h; Michael addition; optical yield given as %ee; enantioselective reaction;
95%
With C12H21N4O2(1+)*Cl(1-); triethylamine In methanol at 20℃; for 36h; Michael Addition; enantioselective reaction;95%
1-methylindole
603-76-9

1-methylindole

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

3-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-1-methyl-1H-indole

3-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-1-methyl-1H-indole

3-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-1-methyl-1H-indole

3-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-1-methyl-1H-indole

Conditions
ConditionsYield
With 1-((1S,2S)-2-aminocyclohexyl)-3-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)thiourea; zinc trifluoromethanesulfonate In toluene at 35℃; for 3h; Friedel-Crafts Alkylation; Inert atmosphere; enantioselective reaction;A 99%
B n/a
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

1,3,5-tris(benzo[d][1,3]dioxol-5-yl)benzene

1,3,5-tris(benzo[d][1,3]dioxol-5-yl)benzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.2h; Sealed tube;98%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

C21H25O6P

C21H25O6P

C25H22NO7P

C25H22NO7P

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; C41H50N4O2P2 In toluene at 40℃; for 24h; stereoselective reaction;98%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

butyraldehyde
123-72-8

butyraldehyde

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-ethyl-4-nitrobutanal

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-ethyl-4-nitrobutanal

Conditions
ConditionsYield
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With 4-methyl-morpholine; C25H31F6N5O2S*C2HF3O2; benzoic acid In dichloromethane at -10℃; for 0.166667h; Michael Addition; Inert atmosphere;
Stage #2: butyraldehyde In dichloromethane at -10 - 20℃; Inert atmosphere; enantioselective reaction;
97%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

3-(3-chlorophenyl)propanal
136415-83-3

3-(3-chlorophenyl)propanal

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-(3-chlorobenzyl)-4-nitrobutanal

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-(3-chlorobenzyl)-4-nitrobutanal

Conditions
ConditionsYield
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With 4-methyl-morpholine; C25H31F6N5O2S*C2HF3O2; benzoic acid In dichloromethane at -10℃; for 0.166667h; Michael Addition; Inert atmosphere;
Stage #2: 3-(3-chlorophenyl)propanal In dichloromethane at -10 - 20℃; Inert atmosphere; enantioselective reaction;
97%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

3-(4-methoxyphenyl)propional
20401-88-1

3-(4-methoxyphenyl)propional

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-(4-methoxybenzyl)-4-nitrobutanal

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-(4-methoxybenzyl)-4-nitrobutanal

Conditions
ConditionsYield
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With 4-methyl-morpholine; C25H31F6N5O2S*C2HF3O2; benzoic acid In dichloromethane at -10℃; for 0.166667h; Michael Addition; Inert atmosphere;
Stage #2: 3-(4-methoxyphenyl)propional In dichloromethane at -10 - 20℃; Inert atmosphere; enantioselective reaction;
97%
prop-2-ene-1-thiol
870-23-5

prop-2-ene-1-thiol

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

2-(allylthio)-2-(3,4-(methylenedioxy)phenyl)-1-nitroethane
128869-28-3

2-(allylthio)-2-(3,4-(methylenedioxy)phenyl)-1-nitroethane

Conditions
ConditionsYield
With piperidine In diethyl ether96%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

butyraldehyde
123-72-8

butyraldehyde

(2R,3S)-3-(benzo[d][1,3]dioxol-5-yl)-2-ethyl-4-nitrobutyraldehyde
1241905-72-5

(2R,3S)-3-(benzo[d][1,3]dioxol-5-yl)-2-ethyl-4-nitrobutyraldehyde

Conditions
ConditionsYield
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With benzoic acid; <(S)-2'-hydroxymethylpyrrolidinyl-N'-carboxy>-(S)-proline In dichloromethane at -20℃; for 0.333333h; Michael addition;
Stage #2: butyraldehyde In dichloromethane at -20℃; for 60h; Michael addition; optical yield given as %ee; enantioselective reaction;
96%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

isovaleraldehyde
590-86-3

isovaleraldehyde

A

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-isopropyl-4-nitrobutanal

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-isopropyl-4-nitrobutanal

B

C14H17NO5

C14H17NO5

Conditions
ConditionsYield
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With 4-methyl-morpholine; C25H31F6N5O2S*C2HF3O2; benzoic acid In dichloromethane at -10℃; for 0.166667h; Michael Addition; Inert atmosphere;
Stage #2: isovaleraldehyde In dichloromethane at -10 - 20℃; Inert atmosphere; enantioselective reaction;
A 96%
B n/a
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

4-Methoxycarbonyl-buten-(3)-yl-(1)-malonsaeurediaethylester
17171-26-5

4-Methoxycarbonyl-buten-(3)-yl-(1)-malonsaeurediaethylester

A

diethyl 2-(benzo[d][1,3]dioxol-5-yl)-4-(2-methoxy-2-oxoethyl)-3-nitrocyclohexane-1,1-dicarboxylate

diethyl 2-(benzo[d][1,3]dioxol-5-yl)-4-(2-methoxy-2-oxoethyl)-3-nitrocyclohexane-1,1-dicarboxylate

B

(2R,3R,4S)-diethyl 2-(benzo[d][1,3]dioxol-5-yl)-4-(2-methoxy-2-oxoethyl)-3-nitrocyclohexane-1,1-dicarboxylate
1408234-32-1

(2R,3R,4S)-diethyl 2-(benzo[d][1,3]dioxol-5-yl)-4-(2-methoxy-2-oxoethyl)-3-nitrocyclohexane-1,1-dicarboxylate

Conditions
ConditionsYield
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea In toluene at 20℃; for 360h; Overall yield = 95 %; Overall yield = 88.4 mg; stereoselective reaction;A n/a
B 95%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

methyl 1-acetyl-3-oxoindoline-2-carboxylate
143466-17-5

methyl 1-acetyl-3-oxoindoline-2-carboxylate

(S)-methyl 1-acetyl-2-((S)-1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-3-oxoindoline-2-carboxylate
1415352-26-9

(S)-methyl 1-acetyl-2-((S)-1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-3-oxoindoline-2-carboxylate

Conditions
ConditionsYield
With C30H29F6N3OS In dichloromethane at 0℃; for 24h; Reagent/catalyst; Solvent; Time; Michael Addition; enantioselective reaction;95%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

dimethyl (prop-2-yn-1-yl)malonate
95124-07-5

dimethyl (prop-2-yn-1-yl)malonate

dimethyl 2-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-2-(prop-2-yn-1-yl)malonate

dimethyl 2-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-2-(prop-2-yn-1-yl)malonate

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -78℃; for 4h; Inert atmosphere;95%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

C8H12O3

C8H12O3

C17H19NO7

C17H19NO7

Conditions
ConditionsYield
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With C34H34FeN4O3 In dichloromethane for 0.0833333h; Michael Addition; Inert atmosphere;
Stage #2: C8H12O3 In dichloromethane at 20℃; for 4h; Michael Addition; Inert atmosphere;
94%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

Benzimidazol-2-thiol
134469-07-1

Benzimidazol-2-thiol

3-(benzo[d][1,3]dioxol-5-yl)benzo[4,5]imidazo[2,1-b]thiazole

3-(benzo[d][1,3]dioxol-5-yl)benzo[4,5]imidazo[2,1-b]thiazole

Conditions
ConditionsYield
With copper(II) acetate monohydrate In N,N-dimethyl-formamide at 80℃; for 8h;94%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

4-(benzo[d][1,3]dioxol-5-yl)-1H-1,2,3-triazole
369363-79-1

4-(benzo[d][1,3]dioxol-5-yl)-1H-1,2,3-triazole

Conditions
ConditionsYield
With sodium azide In water Heating; Green chemistry; regioselective reaction;94%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

ethyl (S)-1-((S)-1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-2-oxocyclopentane-1-carboxylate

ethyl (S)-1-((S)-1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-2-oxocyclopentane-1-carboxylate

Conditions
ConditionsYield
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With C50H43CuF3N4O5S In tetrahydrofuran at -20℃; for 0.0833333h; Inert atmosphere;
Stage #2: 2-ethoxycarbonyl-1-cyclopentanone In tetrahydrofuran at -20℃; for 72h; Inert atmosphere; stereoselective reaction;
94%
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-benzyl-4-nitrobutanal

(2S,3R)-3-(benzo[d][1,3]dioxol-5-yl)-2-benzyl-4-nitrobutanal

Conditions
ConditionsYield
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With 4-methyl-morpholine; C25H31F6N5O2S*C2HF3O2; benzoic acid In dichloromethane at -10℃; for 0.166667h; Michael Addition; Inert atmosphere;
Stage #2: 3-phenyl-propionaldehyde In dichloromethane at -10 - 20℃; Inert atmosphere; enantioselective reaction;
94%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

acetone
67-64-1

acetone

(S)-4-(benzo[d][1,3]dioxol-5-yl)-5-nitropentan-2-one
1093846-34-4

(S)-4-(benzo[d][1,3]dioxol-5-yl)-5-nitropentan-2-one

Conditions
ConditionsYield
With (1R,2R)-(-)-N-diphenylthiophosphorylcyclohexane-1,2-diamine; phenol In toluene at 0℃; for 108h; Michael addition; optical yield given as %ee; enantioselective reaction;93%
With N-((1R,2R)-2-amino-1,2-diphenylethyl)-P,P-diphenylphosphinothioic amide In toluene at 20℃; for 36h; asymmetric Michael addition; optical yield given as %ee; enantioselective reaction;90%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

5-(1,2-dicyanoethyl)-1,3-benzodioxole

5-(1,2-dicyanoethyl)-1,3-benzodioxole

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; acetonitrile at 20℃; for 2h; Michael Addition; Inert atmosphere;93%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

1-methyl-5-nitro-1H-indole-2,3-dione
3484-32-0

1-methyl-5-nitro-1H-indole-2,3-dione

L-proline
147-85-3

L-proline

1-methyl-1',5-dinitro-2'-(3,4-methylenedioxyphenyl)-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizin]-2-one

1-methyl-1',5-dinitro-2'-(3,4-methylenedioxyphenyl)-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizin]-2-one

Conditions
ConditionsYield
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole; 1-methyl-5-nitro-1H-indole-2,3-dione With 1,2-propylene cyclic carbonate In water at 90℃; for 0.25h;
Stage #2: L-proline With carbon dioxide In water at 90℃; for 1h; regioselective reaction;
92%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

acetylacetone
123-54-6

acetylacetone

C14H15NO6
1639342-48-5

C14H15NO6

Conditions
ConditionsYield
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole With C34H34FeN4O3 In dichloromethane for 0.0833333h; Michael Addition; Inert atmosphere;
Stage #2: acetylacetone In dichloromethane at 20℃; for 5h; Michael Addition; Inert atmosphere;
91%
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((1S)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In dichloromethane at 20℃; for 24h; Michael Addition;
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

1-methyl-5-nitro-1H-indole-2,3-dione
3484-32-0

1-methyl-5-nitro-1H-indole-2,3-dione

L-proline
147-85-3

L-proline

5-chloro-1-methyl-1'-nitro-2'-(3,4-methylenedioxyphenyl)-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizin]-2-one

5-chloro-1-methyl-1'-nitro-2'-(3,4-methylenedioxyphenyl)-1',2',5',6',7',7a'-hexahydrospiro[indoline-3,3'-pyrrolizin]-2-one

Conditions
ConditionsYield
Stage #1: 5-(2-nitrovinyl)benzo[1,3]dioxole; 1-methyl-5-nitro-1H-indole-2,3-dione With 1,2-propylene cyclic carbonate In water at 90℃; for 0.25h;
Stage #2: L-proline With carbon dioxide In water at 90℃; for 1h; regioselective reaction;
91%
indole
120-72-9

indole

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

3-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-1H-indole

3-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-1H-indole

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In neat (no solvent) at 80℃; for 24h; Michael Addition; Green chemistry;90%
With zinc(II) acetate dihydrate In cyclohexane at 80℃; for 18h; Michael addition;83%
With silica gel at 20℃; for 2.5h; Michael addition; Neat (no solvent);82%
With water at 100℃; for 10h; Un-catalyzed Friedel-Crafts alkylation;64%
at 100℃; for 9h; Friedel Crafts alkylation; Neat (no solvent);63%
indole
120-72-9

indole

5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

(S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-1H-indole
1092516-33-0

(S)-3-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-1H-indole

Conditions
ConditionsYield
With 2‐(((1S,2R)‐2‐hydroxy‐2,3‐dihydro‐1H‐inden‐1‐yl)carbamothioyl)quinolin‐1‐ium tetrakis[3,5‐bis(trifluoromethyl)phenyl]borate In chloroform at 0℃; for 19h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;90%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

C14H15NO8
1542155-34-9

C14H15NO8

Conditions
ConditionsYield
With Cl(1-)*C32H12BF24(1-)*C6H5N2O2(1-)*C42H48CoN6(3+) In [(2)H6]acetone at 0℃; for 24h;90%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

5-(2-nitroethyl)benzo[1,3]dioxole
21473-47-2

5-(2-nitroethyl)benzo[1,3]dioxole

Conditions
ConditionsYield
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane at 0 - 5℃; for 6h;88%
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane at 0℃; for 6h;88%
With magnesium(II) perchlorate; "grafted NADH model" reagent In acetonitrile; benzene at 80℃; for 120h;72%
5-(2-nitrovinyl)benzo[1,3]dioxole
1485-00-3

5-(2-nitrovinyl)benzo[1,3]dioxole

(E)-4-methyl-N-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide
1195694-52-0

(E)-4-methyl-N-(2-(3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide

2-((2S,3R,4S)-2-(benzo[d][1,3]dioxol-5-yl)-1,2,3,4-tetrahydro-3-nitro-1-tosylquinolin-4-yl)-1-phenylethanone
1619985-25-9

2-((2S,3R,4S)-2-(benzo[d][1,3]dioxol-5-yl)-1,2,3,4-tetrahydro-3-nitro-1-tosylquinolin-4-yl)-1-phenylethanone

Conditions
ConditionsYield
Stage #1: 4-methyl-N-(2-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide With 1-(3,5-Bis-trifluoromethyl-phenyl)-3-[(R)-quinolin-4-yl-((2R,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-thiourea In toluene at 0℃; for 0.0833333h;
Stage #2: 5-(2-nitrovinyl)benzo[1,3]dioxole In toluene at 0℃; for 36h; Michael Addition; stereoselective reaction;
88%
Stage #1: 4-methyl-N-(2-((E)-3-oxo-3-phenylprop-1-en-1-yl)phenyl)benzenesulfonamide With C28H26F6N4S In toluene at 0℃; for 0.0833333h;
Stage #2: 5-(2-nitrovinyl)benzo[1,3]dioxole In toluene at 0℃; for 36h; stereoselective reaction;
88%

1485-00-3Relevant articles and documents

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Lange,Hambourger

, p. 3865 (1931)

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Pharmacological characterization of ecstasy synthesis byproducts with recombinant human monoamine transporters

Pifl, Christian,Nagy, Gabor,Berenyi, Sandor,Kattinger, Alexandra,Reither, Harald,Antus, Sandor

, p. 346 - 354 (2005)

Ecstasy samples often contain byproducts of the illegal, uncontrolled synthesis of N-methyl-3,4-methylenedioxy-amphetamine or 3,4-methylenedioxy- methamphetamine (MDMA). MDMA and eight chemically defined byproducts of MDMA synthesis were investigated for their interaction with the primary sites of action of MDMA, namely the human plasmalemmal monamine transporters for norepinephrine, serotonin, and dopamine [(norepinephrine transporter (NET), serotonin transporter (SERT), and dopamine transporter (DAT)]. SKN-MC neuroblastoma and human embryonic kidney cells stably transfected with the transporter cDNA were used for uptake and release experiments. Two of the eight compounds, 1,3-bis (3,4-methylenedioxyphenyl)-2-propanamine (12) and N-formyl-1,3-bis (3,4-methylenedioxyphenyl)-prop-2-yl-amine (13) had uptake inhibitory potencies with IC50 values in the low micromolar range similar to MDMA. Compounds with nitro instead of amino groups and a phenylethenyl instead of a phenylethyl structure or a formamide or acetamide modification had IC50 values beyond 100 μM. MDMA, 12, and 13 were examined for induction of carrier-mediated release by superfusion of transporter expressing cells preloaded with the metabolically inert transporter substrate [3H]1-methyl-4-phenylpyridinium. MDMA induced release mediated by NET, SERT, or DAT with EC50 values of 0.64, 1.12, and 3.24 μM, respectively. 12 weakly released from NET- and SERT-expressing cells with maximum effects less than one-tenth of that of MDMA and did not release from DAT cells. 13 had no releasing activity. 12 and 13 inhibited release induced by MDMA, and the concentration dependence of this effect correlated with their uptake inhibitory potency at the various transporters. These results do not support a neurotoxic potential of the examined ecstasy synthesis byproducts and provide interesting structure-activity relationships on the transporters. Copyright

Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds

Betancur-Galvis, Liliana,Brand, Yaneth M.,Casta?o, Verónica T.,Kouznetsov, Vladimir V.,Linares, Vicky C. R.,Puerto, Carlos E.

, p. 999 - 1010 (2020)

The design of a series of styrene and spiroisatin hybrids was based on the structure of combretastatin A-4 1. This library of 20 compounds were synthesized with the pharmacophoric units: 3,4,5-trimethoxy or/and 4-hydroxy-3-methoxy phenyl moities in their structure. Thereby, the libraries of β-nitrostyrenes 10a-10c, spiroisatin-dihydroquinolines 14a-14c, spiroisatinthiazolidinones 17a-17c and spiroisatin-nitropyrrolizidines 20a-20k were evaluated for their in vitro cytotoxic, anti-proliferative, antifungal and antiviral activities. Biological results revealed that among these compounds, β-nitrostyrenes 10a-10c exhibited significant cytotoxicity (HeLa and Jurkat tumor cells) and antifungal (T. mentagrophytes) activities. Moreover, the spiroisatin-dihydroquinoline 14a and 14c showed promising cytotoxicity (U937 cells). 14a-14c molecules were active against human herpesviruses serotypes 1 and 2 (HHV-1 and HHV-2), but only 14a and 14b were effective against dengue virus serotype 2 (DENV-2). The spiroisatin-nitropyrrolizidine 20c exhibited moderate anti-herpetic activity, while 17c spiroisatin-thiazolidinone derivative also reduced the infection of HHV-1 and DENV-2. Finally, the molecular docking showed that these kind of molecules interact with the subunit α/β-tubulin.

Berberine derivatives, preparation method thereof and application of berberine derivatives as p300 HAT small molecule inhibitor

-

Paragraph 0048-0051, (2021/02/10)

The invention discloses berberine derivatives, a preparation method thereof and an application of the berberine derivatives as a p300 HAT small molecule inhibitor, and belongs to the technical field of medicinal chemistry. An effective component berberine hydrochloride in a natural product coptis chinensis is taken as a research object and is subjected to structural modification and transformationso as to obtain a series of berberine hydrochloride derivatives. The berberine derivatives have the characteristics of high activity, high selectivity and high safety for p300 HAT, and solves the problems of high cytotoxicity, weak affinity, low activity and poor selectivity of existing p300 HAT small molecule inhibitors.

A method of synthesis of piperonolamine

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Paragraph 0112; 0122-0124; 0128; 0138-0140; 0144; 0151; ..., (2022/01/07)

The present invention belongs to the field of organic chemical synthesis, specifically relates to a synthesis method of piperine, comprising: using catechol as a raw material to prepare piperonaldehyde; β - nitro-3,4-dioxenosylstyrene prepared with piperonaldehyde; β - nitro -3,4-dioxenesimethylenestyrene to obtain piperine ethylamine. Among them, the preparation of piperaldehyde from catechol as raw materials includes two ways: (1) catechol→3,4-dihydroxymandelic acid→3,4-dihydroxybenzaldehyde→ piperaldehyde; (2) catechol→ piperine ring → piperine. The raw materials used in the present invention are safe and readily available, low cost; the reaction conditions are mild, the operation is simple, the chemical yield is high, and the intermediate reagents are easy to recover; suitable for industrial production.

Synthesis, antimicrobial study, and molecular docking simulation of 3,4-dimethoxy-β-nitrostyrene derivatives as candidate ptp1b inhibitor

Alfarisi, Salman,Santoso, Mardi,Kristanti, Alfinda Novi,Siswanto, Imam,Puspaningsih, Ni Nyoman Tri

, p. 1 - 14 (2020/09/09)

A derivative series of 3,4-dimethoxy-β-nitrostyrene was synthesized through nitroaldol reaction, including a new compound of 3,4-ethylenedioxy-β-bromo-β-nitrostyrene. The antimicrobial activity effect of 3,4-alkyloxy modification of β-nitrostyrene was investigated. A molecular docking study was also performed to obtain information about their interactions with protein tyrosine phosphatase 1B (PTP1B). The active residues of cysteine-215 and arginine-221 of PTP1B play a key role in signaling pathways that regulate various microorganism cell functions. It also acts as a negative regulator in signaling pathways of insulin that are involved in type 2 diabetes and other metabolic diseases. These derivatives exhibited potential antifungal activity. The studied compounds were also had potential as fragments to be PTP1B inhibitors by interacting with serine-216 and arginine-221 residues, according to their molecular docking. 3,4-Ethylenedioxy-β-methyl-β-nitrostyrene was the most successful potential candidate as a PTP1B inhibitor. However, further research is needed to investigate their potential for medicinal use.

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