110351-92-3

Basic information

• Product Name: 20R-Camptothecin
• Synonyms: (R)-(-)-Camptothecin;(R)-(-)-Camptothecine;(R)-4-Ethyl-4-hydroxy-1H-pyrano[3’,4’:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;(R)-Camptothecin;20R-Camptothecin;(4R)-4β-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• CAS NO: 110351-92-3
• Molecular Formula: C₂₀H₁₆N₂O₄
• Molecular Weight: 348.35204
• Product Categories: Chiral Reagents;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 110351-92-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 757°Cat760mmHg
• Flash Point: 411.6°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 4.39E-24mmHg at 25°C
• Refractive Index: 1.746
• PKA: 11.24±0.20(Predicted)
• CAS DataBase Reference: 20R-Camptothecin(CAS DataBase Reference)
• NIST Chemistry Reference: 20R-Camptothecin(110351-92-3)
• EPA Substance Registry System: 20R-Camptothecin(110351-92-3)

Safety Data

• Hazardous Substances Data: 110351-92-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 110351-92-3 differently. You can refer to the following data:
1. Antitumor alkaloid. Binds irreversible to the DNA-topoisomerase I complex, inhibiting the reassociation of DNA after cleavage by topoisomerase I and traps the enzyme in a covalent linkage with DNA. A cytotoxic antitumor agent
2. Antitumor alkaloid. Binds irreversible to the DNA-topoisomerase I complex, inhibiting the reassociation of DNA after cleavage by topoisomerase I and traps the enzyme in a covalent linkage with DNA. A cytotoxic antitumor agent.

InChI:InChI=1/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m1/s1

Upstream product

• 26717-67-9 dimethyl ethylmalonate 
• 53821-46-8 methyl 3-methylquinoline-2-carboxylate 
• 54934-04-2 2-Carbomethoxy-3-brommethylchinolin 
• 34141-35-0 4-ethyl-1,12-dihydro-14-H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H)-dione 
• 80231-40-9 2-iodo-3-quinolinecarboxaldehyde 
• 73568-25-9 2-chloro-3-quinoline carboxaldehyde 
• 103-84-4 Acetanilid 
• 694452-80-7 ethyl 2-(2-benzyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-3-yl)acetate 
• 57876-69-4 2-chloro-3-methyl-quinoline 
• 174092-78-5 (S)-(+)-4-ethyl-4-hydroxy-8-methoxy-6-(trimethylsilyl)-1,4-dihydro-3H-pyrano[3,4-c]pyridin-3-one 
• 174092-79-6 (S)-4-ethyl-4-hydroxy-6-iodo-8-methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one 

Relevant articles and documents

Synthesis of indolizinoquinolinones through three- and four-component domino Knoevenagel / hetero-Diels–Alder reactions: novel access to (+)-camptothecin

[Figure not available: see fulltext.] The fused heterocyclic indolizinoquinolinone system is a key structural feature of several highly bioactive alkaloids, including camptothecin. Camptothecin has been efficiently obtained by a three- or four-component domino Knoevenagel / hetero-Diels–Alder reaction of aldehyde, Meldrum's acid, and enol ether in the presence or absence of alcohol, followed by reductive cleavage of the amine protecting group. The obtained products were further transformed along several different routes leading to camptothecin.

Highly efficient and mild cascade reactions triggered by bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate and a concise total synthesis of camptothecin

A mild and efficient cascade methodology is reported to construct variously substituted indolizino[1,2-b]quinolin-9(11H)-ones. Efficiently triggered by bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate under mild conditions, this cascade achieved significant enhancements in chemical yields. Utilizing this highly efficient domino reaction followed by a Sharpless dihydroxylation, an eight-step total synthesis of camptothecln was accomplished from a known pyridine derivative in direct fashion with an overall yield of 47% and 95% ee.

Totalsynthese von (+)-Camptothecin

Keywords: Alkaloide; Asymmetrische Synthesen; Camptothecin; Naturstoffe