1304788-27-9

Basic information

• Product Name: (4S)-4,9-Bis(acetyloxy)-10-[(acetyloxy)Methyl]-4-ethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• Synonyms: (4S)-4,9-Bis(acetyloxy)-10-[(acetyloxy)Methyl]-4-ethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• CAS NO: 1304788-27-9
• Molecular Formula: C27H24N2O9
• Molecular Weight: 520.48746
• Product Categories: Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1304788-27-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Solubility: DMSO, Methanol, Water
• CAS DataBase Reference: (4S)-4,9-Bis(acetyloxy)-10-[(acetyloxy)Methyl]-4-ethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4,9-Bis(acetyloxy)-10-[(acetyloxy)Methyl]-4-ethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione(1304788-27-9)
• EPA Substance Registry System: (4S)-4,9-Bis(acetyloxy)-10-[(acetyloxy)Methyl]-4-ethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione(1304788-27-9)

Safety Data

• Hazardous Substances Data: 1304788-27-9(Hazardous Substances Data)

Usage

Uses

(4S)-4,9-Bis(acetyloxy)-10-[(acetyloxy)methyl]-4-ethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione is an intermediate in the synthesis of Camptothecin analogs for the inhibition of topoisomerase I and antitumor activity.

Upstream product

• 108-24-7 acetic anhydride 
• 123948-87-8 topotecan 

Relevant articles and documents

The solvolysis of topotecan in alcohols and acetic anhydride

Six derivatives of 10-hydroxycamptothecin were prepared via solvolysis of topotecan in corresponding alcohols and acetic anhydride. We attributed the specific reactivity of topotecan to the internal hydrogen-bonding between 10-hydroxy and the nitrogen atom in position 9. As a result the reaction underwent through an intermediate ortho-quionomethlide species to reach equilibrium. Bioactivity screening data showed all products could potentially inhibit the proliferation of several cancer cell lines in vitro and a bigger size group in 9-position would be favorable for the anti-tumor activities observably.