Synthesis and Biological Evaluation of New (−)-Gossypol-Derived Schiff Bases and Hydrazones

A series of 14 new (-)-gossypol Schiff bases and hydrazones have been synthesized via an in situ procedure in high yields. Structural data showed that all target compounds exist as the enamine tautomer. Bioassays showed that several compounds exhibited cytotoxic effects against three human cancer ce...

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Main Authors: Vu Van Vu, Trinh Thi Nhung, Nguyen Thi Thanh, Luu Van Chinh, Vu Dinh Tien, Vu Thu Thuy, Do Thi Thao, Nguyen Hai Nam, Angela Koeckritz, Tran Khac Vu
Format: Article
Language:English
Published: Wiley 2017-01-01
Series:Journal of Chemistry
Online Access:http://dx.doi.org/10.1155/2017/3687182
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author Vu Van Vu
Trinh Thi Nhung
Nguyen Thi Thanh
Luu Van Chinh
Vu Dinh Tien
Vu Thu Thuy
Do Thi Thao
Nguyen Hai Nam
Angela Koeckritz
Tran Khac Vu
author_facet Vu Van Vu
Trinh Thi Nhung
Nguyen Thi Thanh
Luu Van Chinh
Vu Dinh Tien
Vu Thu Thuy
Do Thi Thao
Nguyen Hai Nam
Angela Koeckritz
Tran Khac Vu
author_sort Vu Van Vu
collection DOAJ
description A series of 14 new (-)-gossypol Schiff bases and hydrazones have been synthesized via an in situ procedure in high yields. Structural data showed that all target compounds exist as the enamine tautomer. Bioassays showed that several compounds exhibited cytotoxic effects against three human cancer cell lines. Compound 8a showed the greatest cytotoxic effect against hepatocellular carcinoma (HepG2), lung carcinoma (LU-1), and breast cancer (MCF-7) cell lines with IC50 values of 20.93, 13.58, and 9.40 μM, respectively. However, in an antibacterial test, compounds 8a and 8b inhibited Staphylococcus aureus and Bacillus cereus and compound 8e inhibited only Staphylococcus aureus at the same MIC values of 1024 μg/ml.
format Article
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institution Kabale University
issn 2090-9063
2090-9071
language English
publishDate 2017-01-01
publisher Wiley
record_format Article
series Journal of Chemistry
spelling doaj-art-2b39cd247f874222b32549bcc59600c92025-02-03T05:46:47ZengWileyJournal of Chemistry2090-90632090-90712017-01-01201710.1155/2017/36871823687182Synthesis and Biological Evaluation of New (−)-Gossypol-Derived Schiff Bases and HydrazonesVu Van Vu0Trinh Thi Nhung1Nguyen Thi Thanh2Luu Van Chinh3Vu Dinh Tien4Vu Thu Thuy5Do Thi Thao6Nguyen Hai Nam7Angela Koeckritz8Tran Khac Vu9School of Chemical Engineering, Hanoi University of Science and Technology, No. 1 Dai Co Viet, Hai Ba Trung, Hanoi, VietnamSchool of Chemical Engineering, Hanoi University of Science and Technology, No. 1 Dai Co Viet, Hai Ba Trung, Hanoi, VietnamSchool of Chemical Engineering, Hanoi University of Science and Technology, No. 1 Dai Co Viet, Hai Ba Trung, Hanoi, VietnamInstitute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, VietnamSchool of Chemical Engineering, Hanoi University of Science and Technology, No. 1 Dai Co Viet, Hai Ba Trung, Hanoi, VietnamSchool of Chemical Engineering, Hanoi University of Science and Technology, No. 1 Dai Co Viet, Hai Ba Trung, Hanoi, VietnamInstitute of Biotechnology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, VietnamHanoi University of Pharmacy (HUP), 13-15 Le Thanh Tong, Hanoi, VietnamLeibniz Institute for Catalysis at the University of Rostock, Albert-Einstein-Str. 29A, 18059 Rostock, GermanySchool of Chemical Engineering, Hanoi University of Science and Technology, No. 1 Dai Co Viet, Hai Ba Trung, Hanoi, VietnamA series of 14 new (-)-gossypol Schiff bases and hydrazones have been synthesized via an in situ procedure in high yields. Structural data showed that all target compounds exist as the enamine tautomer. Bioassays showed that several compounds exhibited cytotoxic effects against three human cancer cell lines. Compound 8a showed the greatest cytotoxic effect against hepatocellular carcinoma (HepG2), lung carcinoma (LU-1), and breast cancer (MCF-7) cell lines with IC50 values of 20.93, 13.58, and 9.40 μM, respectively. However, in an antibacterial test, compounds 8a and 8b inhibited Staphylococcus aureus and Bacillus cereus and compound 8e inhibited only Staphylococcus aureus at the same MIC values of 1024 μg/ml.http://dx.doi.org/10.1155/2017/3687182
spellingShingle Vu Van Vu
Trinh Thi Nhung
Nguyen Thi Thanh
Luu Van Chinh
Vu Dinh Tien
Vu Thu Thuy
Do Thi Thao
Nguyen Hai Nam
Angela Koeckritz
Tran Khac Vu
Synthesis and Biological Evaluation of New (−)-Gossypol-Derived Schiff Bases and Hydrazones
Journal of Chemistry
title Synthesis and Biological Evaluation of New (−)-Gossypol-Derived Schiff Bases and Hydrazones
title_full Synthesis and Biological Evaluation of New (−)-Gossypol-Derived Schiff Bases and Hydrazones
title_fullStr Synthesis and Biological Evaluation of New (−)-Gossypol-Derived Schiff Bases and Hydrazones
title_full_unstemmed Synthesis and Biological Evaluation of New (−)-Gossypol-Derived Schiff Bases and Hydrazones
title_short Synthesis and Biological Evaluation of New (−)-Gossypol-Derived Schiff Bases and Hydrazones
title_sort synthesis and biological evaluation of new gossypol derived schiff bases and hydrazones
url http://dx.doi.org/10.1155/2017/3687182
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