84573-33-1

Basic information

• Product Name: quinocarcin
• Synonyms: quinocarcin;(2aR)-11-Methoxy-12-methyl-3β,6β-epimino-2aβ,3,4,5,6,6aβ,7,11bβ-octahydro-2-oxa-11c-aza-1H-naphtho[1,2,3-cd]azulene-5β-carboxylic acid;Quinocarmycin
• CAS NO: 84573-33-1
• Molecular Formula: C20H26N2O4
• Molecular Weight: 358.435
• Mol File: 84573-33-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 521.3°Cat760mmHg
• Flash Point: 269.1°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 1.08E-11mmHg at 25°C
• Refractive Index: 1.665
• CAS DataBase Reference: quinocarcin(CAS DataBase Reference)
• NIST Chemistry Reference: quinocarcin(84573-33-1)
• EPA Substance Registry System: quinocarcin(84573-33-1)

Safety Data

• Hazardous Substances Data: 84573-33-1(Hazardous Substances Data)

Usage

Description

Quinocarcin, also known as (-)-Quinocarcin, is a potent antitumor antibiotic that plays a key role in the construction of the tetracyclic THIQ-pyrrolidine core scaffold. It is a promising pharmaceutical candidate for various applications in the field of cancer treatment.

Uses

Used in Anticancer Applications:
Quinocarcin is used as an anticancer agent for its potent antitumor properties. It is particularly effective against various types of cancer, including solid malignancies. The tetracyclic THIQ-pyrrolidine core scaffold, which is constructed with the help of quinocarcin, is a crucial component in the development of novel anticancer drugs.
Used in Pharmaceutical Industry:
Quinocarcin is used as a key component in the development of new pharmaceuticals for cancer treatment. Its unique structure and potent antitumor properties make it an essential building block for the creation of innovative and effective cancer therapies.

InChI:InChI=1/C18H22N2O4/c1-19-12-7-10(18(21)22)16(19)11-6-9-4-3-5-14(23-2)15(9)13-8-24-17(12)20(11)13/h3-5,10-13,16-17H,6-8H2,1-2H3,(H,21,22)/t10-,11+,12+,13+,16-,17-/m1/s1

Upstream product

• 96251-59-1 4-cyano-6-hydroxymethyl-3,12-imino-7-methoxy-13-methyl-1,2,3,4,6,11,11a,12-octahydroazepino<1,2-b>isoquinoline-1-carboxylic acid 
• 497181-30-3 7-cyanoquinocarcinol 
• 96251-59-1 <5R-(5α,7β,8β,10β,11β,11aβ)>-7-cyano-5,7,8,9,10,11,11a,12-octahydro-4-methoxy-5-(hydroxymethyl)-13-methyl-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid 
• 38197-43-2 2-bromo-3-methylanisole 
• 152500-42-0 2-<(4S,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methylanisole 
• 152500-43-1 2-<(4S,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methylanisole 
• 152500-41-9 2-<(4R,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-3-methylanisole 
• 152500-56-6 (1R,3R)-2,2,2-trichloroethyl 1-acetoxymethyl-3-<(2R,3R,5S)-1-tert-butoxycarbonyl-5-formyl-3-methoxymethoxymethylpyrrolidin-2-yl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate 
• 152500-50-0 (1R,3R)-3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 152500-47-5 3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>-8-methoxyisoquinoline 
• 152500-53-3 (1R,3R)-2,2,2-trichloroethyl 3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-hydroxymethyl-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate 
• 152500-45-3 (2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-<2-<(4S,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbonyl>acetyl>-3-methoxymethoxymethylpyrrolidine 
• 1026239-89-3 (1R,3R)-2,2,2-trichloroethyl 1-acetoxymethyl-3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate 
• 152500-51-1 (1R,3R)-2,2,2-trichloroethyl 3-<(2R,3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethoxymethylpyrrolidin-2-yl>-1-<(4R,5R)-5-methoxymethoxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate 

Downstream Products

• 96251-59-1 4-cyano-6-hydroxymethyl-3,12-imino-7-methoxy-13-methyl-1,2,3,4,6,11,11a,12-octahydroazepino<1,2-b>isoquinoline-1-carboxylic acid 

Relevant articles and documents

Total synthesis of (-)-quinocarcin by gold(I)-catalyzed regioselective hydroamination

In control: The novel and enantioselective total synthesis of (-)-quinocarcin includes the highly stereoselective preparation of the 2,5-cis-pyrrolidine by intramolecular amination, a selective substrate-controlled 6-endo-dig intramolecular alkyne hydroamination with a cationic AuI catalyst, and Lewis-acid-mediated ring-opening/ halogenation sequence. Copyright

Asymmetric total synthesis of (-)-quinocarcin

(-)-Quinocarcin (1) has been synthesized in a longest linear sequence of 22 steps from 3-hydroxybenzaldehyde in 16% overall yield. The Pictet-Spengler reaction of L-tert-butyl-2-bromo-5-hydroxy phenylalanate (17), synthesized according to Corey-Lygo's enantioselective alkylation process, with benzoxyacetaldehyde (12) under mild acidic conditions afforded 1,3-cis tetrahydroisoquinoline 20 as an only isolable stereomer in 91% yield. The diazabicycle[3,2,1]-octane ring system of 28 was constructed by a silver tetrafluoroborate-promoted intramolecular Mannich reaction using amino thioether as a latent N-acyliminium species and tethered silyl enol ether as a nucleophile. Using amino thioether instead of aminal as a precursor of N-acyliminium was of high importance to the success of this otherwise disfavored 5-endo-Trig cyclization. A Hf(OTf)4-catalyzed (0.1 equiv) transformation of aminal to amino thioether was uncovered in the course of this study, allowing the conversion of tricyclic aminal 24 to amino thioether 25 to be realized in high yield. From the bridged tetracyclic compound 28, a sequence of oxidation of aldehyde to acid, global deprotection under hydrogenolysis conditions, and one-pot partial reduction of lactam to aminal/oxazolidine formation completed the total synthesis of the pentacyclic (-)-quinocarcine.

Total Synthesis of (-)-Quinocarcin and (-)-10-Decarboxyquinocarcin

The title total synthesis was accomplished by employing diastereoselective reduction of 1,3-disubstituted isoquinolines as a key step.The cytotoxicity of 10-decarboxyquinocarcin and its 7-cyano congeners were found to be 10-1000 times more potent than tho