40041-96-1

Basic information

• Product Name: Angustine
• Synonyms: Angustine;1-Vinyl-8,13-dihydroindolo[2',3':3,4]pyrido[1,2-b][2,7]naphthyridin-5(7H)-one
• CAS NO: 40041-96-1
• Molecular Formula: C20H15 N3O
• Molecular Weight: 313.3526
• Mol File: 40041-96-1.mol

Chemical Properties

• Boiling Point: 648.2°Cat760mmHg
• Flash Point: 345.8°C
• Appearance: /
• Density: 1.4g/cm³
• CAS DataBase Reference: Angustine(CAS DataBase Reference)
• NIST Chemistry Reference: Angustine(40041-96-1)
• EPA Substance Registry System: Angustine(40041-96-1)

Safety Data

• Hazardous Substances Data: 40041-96-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Angustine is used as a chemotherapeutic agent for its potent anticancer properties. It works by inhibiting DNA and RNA synthesis, leading to the disruption of cellular processes and ultimately causing cell death. This makes it a valuable compound in the development of cancer treatments.
Used in Research and Development:
Angustine is also used as a research tool in the field of oncology, helping scientists understand the mechanisms of cancer cell growth and the potential for targeted therapies. Its study contributes to the advancement of knowledge in cancer biology and the development of novel treatment strategies.
Used in Drug Delivery Systems:
Similar to gallotannin, angustine can be incorporated into drug delivery systems to improve its bioavailability, targeting, and therapeutic outcomes. These systems may include nanoparticles, liposomes, or other advanced drug carriers designed to enhance the efficacy and safety of angustine in cancer treatment.

References

Kametani et ai., Heterocycles, 3, (8) 627 (1975)

Upstream product

• 3430-23-7 3,5-dibromo-4-methyl-pyridine 
• 105-39-5 chloroacetic acid ethyl ester 
• 4894-26-2 3,4-dihydro-β-carboline 
• 57110-40-4 5-ethenyl-4-methyl-3-pyridinecarbonitrile 
• 116965-54-9 11-Vinyl-5,12,12a,13-tetrahydro-6H-6a,9,13-triaza-indeno[2,1-a]anthracen-7-ylideneamine 
• 116965-61-8 2,9-bis-(trimethylsilyl)-3,4-dihydropyrido<3,4-b>indolium trifluoromethane sulphonate 
• 62298-35-5 (5-Bromo-pyridin-3-yl)-(1-methylene-1,3,4,9-tetrahydro-β-carbolin-2-yl)-methanone 
• 20826-04-4 5-bromo-3-pyridinecarboxylic acid 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 62298-30-0 20-bromonauclefine 
• 97168-60-0 13b,14-dihydroangustine 

Downstream Products

• 40041-95-0 angustoline 
• 40041-95-0 (+)-angustoline 

Relevant articles and documents

Synthesis of Nauclefine, Angustidine, Angustine, and (+/-)-13b,14-Dihydroangustine

2,9-Bis-(trimethylsilyl)-3,4-dihydropyridoindolium trifluoromethanesulphonate reacts with the lithio derivatives of 3-cyano-4-methylpyridines to generate pentacyclic amidines which, upon hydrolysis and oxidation, produce nauclefine, angustine, and angustidine.

Total synthesis of angustine and angustoline

A short total synthesis of the indolopyridine alkaloids angustine (1) and angustoline (2) has been achieved in five and six steps, respectively. Two key steps for assembly of the pentacyclic core included a Bischler-Napieralski cyclization and a cobalt-catalyzed carbonylative lactamization. A late-stage Mukaiyama hydration allowed the first successful transformation of angustine (1) to angustoline (2).

Preparation method and application of 21-methyl-subditine

The invention discloses a preparation method of a natural product Subditine shown as a formula 1, 21-methyl-subditine shown as a formula 2 and preparation methods thereof. The natural product Subditine and the 21-methyl-subditine are prepared from a higher intermediate through a coupling reaction between bromine atoms and a coupling reagent. The invention achieves full synthesis of the natural product Subditine, and achieves chemical synthesis of the 21-methyl-subditine for the first time. The natural product Subditine can be prepared through a simple oxidation reaction of the 21-methyl-subditine, and an important practical value for the first chemical synthesis of the natural product Subditine is achieved.

A unified synthetic strategy for the indolopyridine alkaloid group

Thermal or acetyl chloride induced cyclization of bromoenamide 10 affords the pentacyclic derivative 12 with high yield and regioselectivity. From this common synthetic intermediate, palladium-catalyzed reactions allow the total synthesis of indolopyridin

Regioselective Syntheses of the Indolopyridine Alkaloids Nauclefine, Angustine, Dihydroangustine and Naucletine from a Common Intermediate

A short, flexible route for the synthesis of the title indolopyridine alkaloids consisting of the cyclization of enamide 3, followed by introduction of the requisite pyridine substituent by Pd0-catalysed reactions from the resulting pentacyclic bromo intermediate 4 is reported.

SYNTHESIS OF NAUCLEFINE, ANGUSTIDINE, ANGUSTINE, (+/-)-13b,14-DIHYDROANGUSTINE AND NAULAFINE

The lithio derivatives of 3-cyano-4-methylpyridines and 6,7-dihydro-5H-2-pyridine-4-carbonitrile react with 2,9-bis-(trimethylsilyl)-3,4-dihydropyridoindolium trifluoromethanesulfonate to form cyclic amidines which, upon hydrolysis and oxidation, produce the title alkaloids.