186668-40-6

Basic information

• Product Name: BN 80245
• Synonyms: BN 80245;(±)-E-Homocamptothecin
• CAS NO: 186668-40-6
• Molecular Formula: C₂₁H₁₈N₂O₄
• Molecular Weight: 362.37862
• EINECS: -0
• Mol File: 186668-40-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BN 80245(CAS DataBase Reference)
• NIST Chemistry Reference: BN 80245(186668-40-6)
• EPA Substance Registry System: BN 80245(186668-40-6)

Safety Data

• Hazardous Substances Data: 186668-40-6(Hazardous Substances Data)

Upstream product

• 186668-38-2 tert-butyl 3-hydroxy-3-(3-hydroxymethyl-4-oxo-4,6-dihydroindolixino<1,2-b>quinolin-2-yl)pentanoate 
• 54318-62-6 (9-oxo-7-propionyl-9,11-dihidroindolizino[1,2-b]quinolin-8-yl)methyl formate 
• 7689-03-4 camptothecin 
• 618-36-0 rac-methylbenzylamine 
• 186668-41-7 3-hydroxy-3-(3-hydroxymethyl-4-oxo-4,6-dihydroindolizino<1,2-b>quinolin-2-yl)pentanoic acid 
• 26908-34-9 N-(2-(1,3-dioxolan-2-yl))phenylamine 
• 863217-08-7 9-ethyl-9-hydroxy-2,3,8,9-tetrahydro-5H-6-oxa-3a-azacyclohepta[f]indene-1,4,7-trione 
• 210563-62-5 (-)-O,21-dihydrocamptothecin 

Downstream Products

• 631090-68-1 homo-camptothecin-20-O-3-[(4-benzyl)-1-piperazinyl]propionate 
• 631090-67-0 homo-camptothecin-20-O-3-[4-(3-trifluoromethylphenyl)-1-piperazinyl]propionate 
• 631090-69-2 homo-camptothecin-20-O-3-[4-(3-methoxyphenyl)-1-piperazinyl]propionate 
• 631090-70-5 homo-camptothecin-20-O-3-[4-(4-nitrophenyl)-1-piperazinyl]propionate 
• 631090-71-6 homo-camptothecin-20-O-3-(4-phenyl-1-piperazinyl)propionate 
• 631090-72-7 homo-camptothecin-20-O-3-[4-(2-chlorophenyl)-1-piperazinyl]propionate 
• 631090-79-4 homo-camptothecin-20-O ester of 4-cyano-4-phenyl-piperidine propionic acid 
• 631090-73-8 homo-camptothecin-20-O-3-[4-(4-fluorophenyl)-1-piperazinyl]propionate 
• 631090-76-1 homo-camptothecin-20-O-3-[4-(4-acetylphenyl)-1-piperazinyl]propionate 
• 631090-75-0 homo-camptothecin-20-O-3-[1-(4-benzyl)piperidino]propionate 
• 1268700-84-0 12-[2-(3-chlorophenyl)ethenyl]-5-ethyl-1,4,5,13-tetrahydro-5-hydroxy-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione 
• 1268700-94-2 5-ethyl-1,4,5,13-tetrahydro-5-hydroxy-12-{2-[2-(trifluoromethyl)phenyl]ethenyl}-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione 
• 1384248-25-2 5-ethyl-1,4,5,13-tetrahydro-5-hydroxy-12-{(Z)-2-[2-(trifluoromethyl)phenyl]ethenyl}-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione 
• 1268700-89-5 5-ethyl-1,4,5,13-tetrahydro-5-hydroxy-12-{2-[4-(trifluoromethyl)phenyl]ethenyl}-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione 

Relevant articles and documents

BN 80245: An E-ring modified camptothecin with potent antiproliferative and topoisomerase I inhibitory activities

The crucial E-ring of camptothecin has been modified to afford the homologous β-hydroxylactone derivative BN 80245. This compound, which is more stable than camptothecin, remains a potent inhibitor of both cell growth and topoisomerase I.

New homocamptothecins: Synthesis, antitumor activity, and molecular modeling

Homocamptothecins (hCPTs) represent a class of new emerging antitumor agents, which contains a seven-membered β-hydroxylactone in place of the conventional six-membered α-hydroxylactone ring (E ring) of camptothecins. Some novel 7-substituted hCPTs were designed and synthesized based on a newly developed synthetic route which couples ring A with ring C, E and D. Most of the synthesized compounds exhibit very high cytotoxic activity on tumor cell line A549. Some compounds, such as 9b, 9l, and 9y, show broad in vitro antitumor spectrum and are more potent than topotecan. Three-dimensional quantitative structure-activity relationship (3D-QSAR) methods, CoMFA and CoMSIA, were applied to explain the structure-activity relationship (SAR) of the synthesized compounds. Furthermore, molecular docking was used to clarify the binding mode of the synthesized compounds to human DNA topoisomerase I. The important hydrophobic, base-pair stacking, and hydrogen-bonding interactions were observed between the hCPT derivatives and their receptor. The results from molecular modeling will guide the design of novel hCPTs with higher antitumor activity.

New analogues of camptothecin, their use as medicaments and the pharmaceutical compositions containing them

A compound of the formula wherein the substituents are defined as in the specification which compounds are useful in the treatment of cancer.