7305-71-7

Basic information

• Product Name: 2-Amino-5-methylthiazole
• Synonyms: 2-Amino-5-methylthiazole ,99%;Meloxicam Related Compound B (25 mg) (2-Amino-5-methyl-thiazole);2-Amino-5-methylthia;5-Methyl-1,3-thiazol-2-ylaMine;5-Methyl-2-aMinothiazole;NSC 523150;2-Amino-5-methyl-1,3-thiazole;Meloxicam EP Impurity B
• CAS NO: 7305-71-7
• Molecular Formula: C₄H₆N₂S
• Molecular Weight: 114.17
• EINECS: 423-800-5
• Product Categories: Heterocyclic Building Blocks;C3 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Intermediates of Dyes and Pigments;Amines;blocks;Thiazoles;Sulphur Derivatives;INTERMEDIATESOFMELOXICAN;Thiazoles, Isothiazoles &Benzothiazoles;Amino;Building Blocks;Pyrimidine;Organohalides;Thiazoles, Isothiazoles & Benzothiazoles;Building Blocks;2-Amino-5-Methylthiazole sky;18031153937@189.cn
• Mol File: 7305-71-7.mol
• Article Data: 16

Chemical Properties

• Melting Point: 93-98 °C(lit.)
• Boiling Point: 232.5 °C at 760 mmHg
• Flash Point: 94.4 °C
• Appearance: Brown/Powder
• Density: 1.258 g/cm³
• Vapor Pressure: 0.0588mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 5.42±0.10(Predicted)
• BRN: 109603
• CAS DataBase Reference: 2-Amino-5-methylthiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-methylthiazole(7305-71-7)
• EPA Substance Registry System: 2-Amino-5-methylthiazole(7305-71-7)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 22-48/22-50/53-36/37/38
• Safety Statements: 60-61-29-26-37/39
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 7305-71-7(Hazardous Substances Data)

Usage

Description

2-Amino-5-methylthiazole is an aminothiazole derivative characterized by the presence of an amino group at the 2nd position and a methyl group at the 5th position on the thiazole ring. It is known for its ability to form metal complexes that can bind competitively to DNA, making it a valuable compound for characterization and DNA-interaction studies.

Uses

Used in Solar Cell Industry:
2-Amino-5-methylthiazole is used as a component in solar cells to influence the interaction with the TiO2 photoelectrode. This interaction can alter the performance of dye-sensitized solar cells, potentially improving their efficiency and effectiveness in converting sunlight into electricity.
Used in Chemical Synthesis:
2-Amino-5-methylthiazole may be used in the preparation of acrylamide monomer, specifically 5-methyl-2-thiozyl methacrylamide (MTMAAm). This monomer can be polymerized to form polymers with specific properties, which can be utilized in various applications such as water treatment, drug delivery, and material science.

InChI:InChI=1/C4H6N2S/c1-3-2-6-4(5)7-3/h2H,1H3,(H2,5,6)

Synthetic route

methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (35511-15-0) + meloxicam (71125-38-7) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With montmorillonite MK10 impregnated with ZnCl2 In o-xylene for 24h; Reagent/catalyst; Reflux; Green chemistry;	90%

potassium thioacyanate + chloroacetone (78-95-5) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With ammonium acetate on neutral alumina; silica gel In benzene at 80℃; for 6h;	83%

1-isothiocyanatopropa-1,2-diene (137768-73-1) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With ammonia	59%
With ammonium hydroxide In tetrahydrofuran at 20℃; for 72h;	59%

1-isothiocyanatopropa-1,2-diene (137768-73-1) → 5-methyl-2-thiazol-2-amine (7305-71-7) + (5,5'-dimethyl-[2,3'-bithiazolyl]-2'-ylidene)-(5-methylthiazol-2-yl)-amine (137768-80-0) + 5,5'-dimethyl-2'-imino-[2,3'-bithiazolyl] (137768-81-1)

Conditions	Yield
With ammonium hydroxide In tetrahydrofuran at 20℃;	A 11% B 50% C n/a

propan-1-ol (71-23-8) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With chlorine at 8 - 10℃; Behandeln des Reaktionsprodukts mit Thioharnstoff;

propionaldehyde (123-38-6) + thiourea (17356-08-0) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With sulfuryl dichloride
With chloroform; bromine
With chloroform; iodine

2-chloropropanal (683-50-1) + thiourea (17356-08-0) → 5-methyl-2-thiazol-2-amine (7305-71-7)

bromo-2 propanal (19967-57-8) + thiourea (17356-08-0) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
Reaktion des Hydrats;

thiourea (17356-08-0) + 2-bromopropionaldehyde diethyl acetal (3400-55-3) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With hydrogenchloride

thiourea (17356-08-0) + 2-bromo-propionaldehyde-hydrate → 5-methyl-2-thiazol-2-amine (7305-71-7)

phenyl N-2-(5-methylthiazolyl)carbamate (921203-76-1) → 5-methyl-2-thiazol-2-amine (7305-71-7) + phenol (108-95-2)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 25℃; Kinetics;

propionaldehyde (123-38-6) → 5-methyl-2-thiazol-2-amine (7305-71-7)

Conditions	Yield
With sulfuryl dichloride; thiourea In ethanol; chloroform
With sulfuryl dichloride; thiourea In ethanol; chloroform

2-(5-methylthiazol-2-yliminomethyl)phenol → 5-methyl-2-thiazol-2-amine (7305-71-7) + salicylaldehyde (90-02-8)

Conditions	Yield
With aluminium(III) chloride hexahydrate; water In methanol at 20℃; for 2h;

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-(((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)methyl)benzoic acid → 4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylamino)methyl)-N-(5-methylthiazol-2-yl)benzamide

Conditions	Yield
Stage #1: 4-(((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)methyl)benzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Stage #2: 5-methyl-2-thiazol-2-amine In N,N-dimethyl-formamide at 20℃;	98.61%
Stage #1: 4-(((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)methyl)benzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Stage #2: 5-methyl-2-thiazol-2-amine In N,N-dimethyl-formamide at 20℃;	98.61%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

5-methyl-2-thiazol-2-amine (7305-71-7) + 6-chloropyrazine-2-carboxylic acid chloride (148673-71-6) → 6-chloro-pyrazine-2-carboxylic acid (5-methyl-thiazol-2-yl)-amide

Conditions	Yield
With pyridine In acetone at 20℃; for 0.5h;	98%

5-methyl-2-thiazol-2-amine (7305-71-7) + 6-chloro-5-tert-butylpyrazine-2-carboxylic acid chloride (879131-25-6) → 5-tert-butyl-6-chloro-pyrazine-2-carboxylic acid (5-methyl-thiazol-2-yl)-amide

Conditions	Yield
With pyridine In acetone at 20℃; for 0.5h;	98%

5-methyl-2-thiazol-2-amine (7305-71-7) + ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (24683-26-9) → meloxicam (71125-38-7)

Conditions	Yield
In o-xylene for 24h; Product distribution / selectivity; Heating / reflux;	95%
In xylene at 139 - 140℃; for 32 - 37h; Product distribution / selectivity; Heating / reflux; Molecular sieve;	92.48%

5-methyl-2-thiazol-2-amine (7305-71-7) + 5-((4,6-dichloropyrimidin-2-yl)oxy)-4-fluoro-2-methyl-1H-indole (1609119-40-5) → N-(6-chloro-2-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)pyrimidin-4-yl)-5-methylthiazol-2-amine (1609119-46-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide at 70℃;	95%

5-methyl-2-thiazol-2-amine (7305-71-7) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 1-(E)-[(5-methylthiazol-2-ylimino)methyl]naphthalen-2-ol

Conditions	Yield
In methanol for 6h; Reflux;	95%

5-methyl-2-thiazol-2-amine (7305-71-7) + cyanoacetic acid (372-09-8) → 2-cyano-N-(5-methylthiazol-2-yl)acetamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	95%

5-methyl-2-thiazol-2-amine (7305-71-7) + 1,3-thiazole-2-carbonyl chloride (30216-57-0) → N-(2-methylthiazole-5-yl)-thiazole-2-carboxamide (475637-27-5)

Conditions	Yield
With triethylamine; lithium chloride In 1-methyl-pyrrolidin-2-one at 20℃; for 72h;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) + 2-nitrobenzyl chloride (610-14-0) → N-(5-methylthiazol-2-yl)-2-nitrobenzamide

Conditions	Yield
In dichloromethane at 0℃; Inert atmosphere;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) + acetyl chloride (75-36-5) → N-(5-methylthiazol-2-yl)acetamide (61996-32-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; for 2h;	94%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃;

4-methyl-[1,2,3]thiadiazole-5-carbonyl chloride (59944-65-9) + 5-methyl-2-thiazol-2-amine (7305-71-7) → 4-methyl-N-(5'-methyl-1,3-thiazol-2'-yl)-1,2,3-thiadiazole-5-carboxamide

Conditions	Yield
In toluene at 100 - 105℃; for 4h; Solvent; Temperature; Reflux;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 4-chlorobenzaldehyde (104-88-1) → 7-(4-chlorophenyl)-10-methyl-6H,7H-chromeno[4,3-d]thiazolo[3,2-a]pyrimidin-6-one

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 4-chlorobenzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.5h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst; Reflux; Green chemistry;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 3,4 difluorobenzaldehyde (34036-07-2) → C20H12F2N2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 3,4 difluorobenzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.583333h; Reflux; Green chemistry;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) + Pyridine-2,6-dicarboxylic acid (499-83-2) → N2,N6-bis(5-methylthiazol-2-yl)pyridine-2,6-dicarboxamide

Conditions	Yield
Stage #1: 5-methyl-2-thiazol-2-amine; Pyridine-2,6-dicarboxylic acid With pyridine at 120℃; for 0.5h; Stage #2: With triphenyl phosphite at 100 - 120℃; for 6h;	94%

5-methyl-2-thiazol-2-amine (7305-71-7) → 2-chloro-5-methyl-thiazole (33342-65-3)

Conditions	Yield
With t-butyl thionitrite; copper dichloride In acetonitrile at 25℃; for 2.66667h; Inert atmosphere;	93%
With t-butyl thionitrite; copper dichloride In acetonitrile at 25℃; for 2.66667h; Time; Inert atmosphere;	93%
With 2-methylchlorobenzene; copper(l) chloride In hexane at 6 - 65℃; for 15h; Temperature;	81%

5-methyl-2-thiazol-2-amine (7305-71-7) + 2-chloro-6-fluorobenzoic acid (434-75-3) → 6-fluoro-2-methyl-5H-[1,3]-thiazolo[2,3-b]quinazolin-5-one

Conditions	Yield
With copper; potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.25h; sonication;	93%
With copper Ullmann condensation; Sonication;

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-(3-chloro-4-cyanophenoxy)butanoic acid → 4-(3-chloro-4-cyanophenoxy)-N-(5-methylthiazol-2-yl)butanamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 16h;	93%

5-methyl-2-thiazol-2-amine (7305-71-7) + m-nitrobenzoic acid chloride (121-90-4) → N-(5-methylthiazol-2-yl)-3-nitrobenzamide

Conditions	Yield
In dichloromethane at 0℃; Inert atmosphere;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 1-halo-2,4-dinitrobenzene → C10H8N4O4S

Conditions	Yield
With tributyl-amine In N,N-dimethyl-formamide at 100℃; for 12h; Flow reactor;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + benzaldehyde (100-52-7) → C20H14N2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; benzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.5h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 2-chloro-benzaldehyde (89-98-5) → C20H13ClN2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 2-chloro-benzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.583333h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 3-Chlorobenzaldehyde (587-04-2) → C20H13ClN2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; m-Chlorobenzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.5h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + m-bromobenzoic aldehyde (3132-99-8) → C20H13BrN2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; m-bromobenzoic aldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.633333h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 4-methyl-benzaldehyde (104-87-0) → C21H16N2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 4-methyl-benzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.5h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-hydroxy[1]benzopyran-2-one (1076-38-6) + 4-fluorobenzaldehyde (459-57-4) → C20H13FN2O2S

Conditions	Yield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 4-fluorobenzaldehyde at 20℃; Knoevenagel Condensation; Green chemistry; Stage #2: 5-methyl-2-thiazol-2-amine for 0.75h; Reflux; Green chemistry;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 4-(4-chloro-3-methylphenoxy)-2-methylbutanoic acid → 4-(4-chloro-3-methylphenoxy)-2-methyl-N-(5-methylthiazol-2-yl)butanamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 1,2-dichloro-ethane at 45℃; for 16h;	92%

5-methyl-2-thiazol-2-amine (7305-71-7) + 3,4-dichloro-isothiazole-5-carbonyl chloride (56914-82-0) → C8H5Cl2N3OS2

Conditions	Yield
Stage #1: 5-methyl-2-thiazol-2-amine With triethylamine In dichloromethane for 0.166667h; Cooling with ice; Stage #2: 3,4-dichloro-isothiazole-5-carbonyl chloride In dichloromethane at 20℃; for 3h;	91.6%

succinic acid anhydride (108-30-5) + 5-methyl-2-thiazol-2-amine (7305-71-7) → C8H10N2O3S (888125-33-5)

Conditions	Yield
In ethyl acetate at 20℃; for 2h;	91.3%
In tetrahydrofuran at 65℃; for 3h;

5-methyl-2-thiazol-2-amine (7305-71-7) + phthalic anhydride (85-44-9) → 2-(5-methyl-thiazol-2-yl)-isoindole-1,3-dione (832091-87-9)

Conditions	Yield
With triethylamine In toluene at 200℃; for 2h; Sealed tube;	91%
In 1,4-dioxane at 110℃;	56%

5-methyl-2-thiazol-2-amine (7305-71-7) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) → C7H5Cl2N5S (1258205-29-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -5℃; Inert atmosphere;	91%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -5℃;	91%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -5℃;

Upstream product

• 71-23-8 propan-1-ol 
• 123-38-6 propionaldehyde 
• 19967-57-8 bromo-2 propanal 
• 17356-08-0 thiourea 
• 35511-15-0 methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 71125-38-7 meloxicam 
• 137768-73-1 1-isothiocyanatopropa-1,2-diene 
• 921203-76-1 phenyl N-2-(5-methylthiazolyl)carbamate 
• 333-20-0 potassium thioacyanate 
• 78-95-5 chloroacetone 
• 3400-55-3 2-bromopropionaldehyde diethyl acetal 
• 683-50-1 2-chloropropanal 

Downstream Products

• 13738-07-3 N-(5-methyl-thiazol-2-yl)-5-nitro-2-octyloxy-benzamide 
• 39122-64-0 Ethyl-N-(5-methylthiazol-2-yl)carbamat 
• 75793-02-1 2,5-dichloro-3,6-bis-(5-methyl-thiazol-2-ylamino)-[1,4]benzoquinone 
• 107518-43-4 2,5-dimethyl-6-phenyl-imidazo[2,1-b]thiazole 
• 39122-63-9 N-Ethoxycarbonyl-N'-(5-methylthiazol-2-yl)thioharnstoff 
• 51226-37-0 2-methyl-6-phenylimidazo<2,1-b>thiazole 
• 101717-13-9 2-methyl-5,6-diphenyl-imidazo[2,1-b]thiazole 
• 32187-00-1 2-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester 
• 92192-03-5 2-acetoxy-N-(5-methyl-thiazol-2-yl)-2-phenyl-acetamide 
• 27225-15-6 2-fluoro-5-methyl-thiazole 
• 3581-89-3 5-methylthiazole 
• 475108-58-8 N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-phenyl}-N'-(5-methyl-1,3-thiazol-2-yl)urea 
• 475108-54-4 N-{2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-(5-methyl-1,3-thiazol-2-yl)urea 
• 475108-62-4 N-{3-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-(5-methyl-1,3-thiazol-2-yl)urea 

Relevant articles and documents

An innovative and efficient method to synthesize meloxicam in one-step procedure with respect to the green chemistry

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