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Synthesis and biological evaluation of novel homocamptothecins conjugating with dihydropyrimidine derivatives as potent topoisomerase I inhibitors.
Arch Pharm (Weinheim). 2011 Nov; 344(11):726-34.AP

Abstract

Homocamptothecin (hCPT) is a camptothecin (CPT) homologue with the insertion of a methylene (CH₂) spacer between the alcohol moiety and carbonyl group of the classical six-membered α-hydroxylactone ring. This modification provides higher lactone stability and did not impair its activity against topoisomerase I (Topo I), but rather appears to improve it compared to CPT. In an attempt to improve the antitumor activity of homocamptothecins, a series of novel hCPT derivatives conjugating with dihydropyrimidine (DHPM) derivatives was designed and synthesized based on a synthetic route which couples 7-formylhomocamptothecin with different dihydropyrimidine derivates. Most of the synthesized compounds exhibited good antiproliferative activity on tumor cell lines A549, MDA-MB-435 and HCT116. Furthermore, this class of compounds showed superior Topo I inhibition activity comparable to or higher than CPT.

Authors+Show Affiliations

School of Pharmacy, Second Military Medical University, Shanghai, P. R. China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21956522

Citation

Zhu, Lingjian, et al. "Synthesis and Biological Evaluation of Novel Homocamptothecins Conjugating With Dihydropyrimidine Derivatives as Potent Topoisomerase I Inhibitors." Archiv Der Pharmazie, vol. 344, no. 11, 2011, pp. 726-34.
Zhu L, Cheng P, Lei N, et al. Synthesis and biological evaluation of novel homocamptothecins conjugating with dihydropyrimidine derivatives as potent topoisomerase I inhibitors. Arch Pharm (Weinheim). 2011;344(11):726-34.
Zhu, L., Cheng, P., Lei, N., Yao, J., Sheng, C., Zhuang, C., Guo, W., Liu, W., Zhang, Y., Dong, G., Wang, S., Miao, Z., & Zhang, W. (2011). Synthesis and biological evaluation of novel homocamptothecins conjugating with dihydropyrimidine derivatives as potent topoisomerase I inhibitors. Archiv Der Pharmazie, 344(11), 726-34. https://doi.org/10.1002/ardp.201000402
Zhu L, et al. Synthesis and Biological Evaluation of Novel Homocamptothecins Conjugating With Dihydropyrimidine Derivatives as Potent Topoisomerase I Inhibitors. Arch Pharm (Weinheim). 2011;344(11):726-34. PubMed PMID: 21956522.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and biological evaluation of novel homocamptothecins conjugating with dihydropyrimidine derivatives as potent topoisomerase I inhibitors. AU - Zhu,Lingjian, AU - Cheng,Pengfei, AU - Lei,Ning, AU - Yao,Jianzhong, AU - Sheng,Chunquan, AU - Zhuang,Chunlin, AU - Guo,Wei, AU - Liu,Wenfeng, AU - Zhang,Yongqiang, AU - Dong,Guoqiang, AU - Wang,Shengzhang, AU - Miao,Zhenyuan, AU - Zhang,Wannian, Y1 - 2011/09/29/ PY - 2010/12/28/received PY - 2011/02/28/revised PY - 2011/03/02/accepted PY - 2011/9/30/entrez PY - 2011/10/1/pubmed PY - 2012/2/16/medline SP - 726 EP - 34 JF - Archiv der Pharmazie JO - Arch. Pharm. (Weinheim) VL - 344 IS - 11 N2 - Homocamptothecin (hCPT) is a camptothecin (CPT) homologue with the insertion of a methylene (CH₂) spacer between the alcohol moiety and carbonyl group of the classical six-membered α-hydroxylactone ring. This modification provides higher lactone stability and did not impair its activity against topoisomerase I (Topo I), but rather appears to improve it compared to CPT. In an attempt to improve the antitumor activity of homocamptothecins, a series of novel hCPT derivatives conjugating with dihydropyrimidine (DHPM) derivatives was designed and synthesized based on a synthetic route which couples 7-formylhomocamptothecin with different dihydropyrimidine derivates. Most of the synthesized compounds exhibited good antiproliferative activity on tumor cell lines A549, MDA-MB-435 and HCT116. Furthermore, this class of compounds showed superior Topo I inhibition activity comparable to or higher than CPT. SN - 1521-4184 UR - https://www.unboundmedicine.com/medline/citation/21956522/Synthesis_and_biological_evaluation_of_novel_homocamptothecins_conjugating_with_dihydropyrimidine_derivatives_as_potent_topoisomerase_I_inhibitors_ L2 - https://doi.org/10.1002/ardp.201000402 DB - PRIME DP - Unbound Medicine ER -