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Synthesis and antitumor activity of 20(S)-camptothecin derivatives. A-ring-substituted 7-ethylcamptothecins and their E-ring-modified water-soluble derivatives.
Chem Pharm Bull (Tokyo). 1994 Dec; 42(12):2518-25.CP

Abstract

Twenty-six novel A-ring-modified 7-ethylcamptothecins (6) were synthesized by Friedländer's condensation of the chiral tricyclic ketone (5) with aminopropiophenones (4). The compounds substituted with fluorine at the 11 position showed strong cytotoxicity to KB and L1210 cells. The 11-fluoro derivatives also exhibited strong inhibitory activity on DNA topoisomerase I. Nine compounds 6 with four to ten times stronger cytotoxicity than that of camptothecin were selected and converted into water-soluble 17-O-acyl amide derivatives (8). Compounds 8e (10-Me, O-COCH2CH2SCH3) and 8f (11-F, O-COC2H5) showed activity towards Meth A in mice that was comparable to that of CPT-11, at lower doses than CPT-11.

Authors+Show Affiliations

Yakult Central Institute for Microbiological Research, Tokyo, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

7697767

Citation

Yaegashi, T, et al. "Synthesis and Antitumor Activity of 20(S)-camptothecin Derivatives. A-ring-substituted 7-ethylcamptothecins and Their E-ring-modified Water-soluble Derivatives." Chemical & Pharmaceutical Bulletin, vol. 42, no. 12, 1994, pp. 2518-25.
Yaegashi T, Sawada S, Nagata H, et al. Synthesis and antitumor activity of 20(S)-camptothecin derivatives. A-ring-substituted 7-ethylcamptothecins and their E-ring-modified water-soluble derivatives. Chem Pharm Bull. 1994;42(12):2518-25.
Yaegashi, T., Sawada, S., Nagata, H., Furuta, T., Yokokura, T., & Miyasaka, T. (1994). Synthesis and antitumor activity of 20(S)-camptothecin derivatives. A-ring-substituted 7-ethylcamptothecins and their E-ring-modified water-soluble derivatives. Chemical & Pharmaceutical Bulletin, 42(12), 2518-25.
Yaegashi T, et al. Synthesis and Antitumor Activity of 20(S)-camptothecin Derivatives. A-ring-substituted 7-ethylcamptothecins and Their E-ring-modified Water-soluble Derivatives. Chem Pharm Bull. 1994;42(12):2518-25. PubMed PMID: 7697767.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and antitumor activity of 20(S)-camptothecin derivatives. A-ring-substituted 7-ethylcamptothecins and their E-ring-modified water-soluble derivatives. AU - Yaegashi,T, AU - Sawada,S, AU - Nagata,H, AU - Furuta,T, AU - Yokokura,T, AU - Miyasaka,T, PY - 1994/12/1/pubmed PY - 1994/12/1/medline PY - 1994/12/1/entrez SP - 2518 EP - 25 JF - Chemical & pharmaceutical bulletin JO - Chem. Pharm. Bull. VL - 42 IS - 12 N2 - Twenty-six novel A-ring-modified 7-ethylcamptothecins (6) were synthesized by Friedländer's condensation of the chiral tricyclic ketone (5) with aminopropiophenones (4). The compounds substituted with fluorine at the 11 position showed strong cytotoxicity to KB and L1210 cells. The 11-fluoro derivatives also exhibited strong inhibitory activity on DNA topoisomerase I. Nine compounds 6 with four to ten times stronger cytotoxicity than that of camptothecin were selected and converted into water-soluble 17-O-acyl amide derivatives (8). Compounds 8e (10-Me, O-COCH2CH2SCH3) and 8f (11-F, O-COC2H5) showed activity towards Meth A in mice that was comparable to that of CPT-11, at lower doses than CPT-11. SN - 0009-2363 UR - https://www.unboundmedicine.com/medline/citation/7697767/Synthesis_and_antitumor_activity_of_20_S__camptothecin_derivatives__A_ring_substituted_7_ethylcamptothecins_and_their_E_ring_modified_water_soluble_derivatives_ L2 - https://www.lens.org/lens/search?q=citation_id:7697767 DB - PRIME DP - Unbound Medicine ER -