Antitumor agents 281. Design, synthesis, and biological activity of substituted 4-amino-7,8,9,10-tetrahydro-2H-benzo[h]chromen-2-one analogs (ATBO) as potent in vitro anticancer agents

The synthesis and the biological activity towards human neutrophils of some N-formyl-Met-Leu-Phe-OMe analogues containing (S)-phenylalaninol (Pheol) or its derivatives in place of the native phenylalanine are reported. While the analogue containing Pheol (4) was found to be devoid of significant biological activity, its esters 3 and 5, although inactive as chemoattractants, are able to strongly stimulate superoxide production and are active with a lower efficacy in the lysozyme release.

Formyl peptide receptor

Peptide Synthesis

Oligopeptide

10.1002/ardp.19953280908

Cite

Citations (5)

Role of the C8 gem-dimethyl group of bryostatin 1 on its unique pattern of biological activity

Bioorganic & Medicinal Chemistry Letters (2012)

Gary E. Keck Yam B. Poudel Arnab Rudra Jeffrey C. Stephens Noémi Kedei

Bryostatin 1

10.1016/j.bmcl.2012.04.073

Cite

Citations (25)

Structures and Cytotoxicity Relationship of Isoaaptamine and Aaptamine Derivatives

Journal of Natural Products (1999)

Ya‐Ching Shen Tain‐Tsair Lin Jyh‐Horng Sheu Chang‐Yih Duh

A series of 9-O-acylisoaaptamine (3−14) and 4-N-acyl-dihydroaaptamine (16−19) derivatives have been prepared and evaluated for antitumor activity against murine P-388 and human tumor cells including KB16, A549, and HT-29 cell lines. All of compounds showed significant cytotoxicity against P-388 cells. Among them, compounds 9−11 showed potent activity as isoaaptamine (1). There was an apparent lack of linear relationship between cytotoxicity and carbon number of the side chain. The structure and activity relationship for these particular compounds are discussed.

Structure–activity relationship

Chemical structure

10.1021/np990156g

Cite

Citations (39)

New nonpeptide angiostensin II receptor antagonists. Synthesis, biological properties and structure-activity relationships of 3-substituted 2,6-dialkyl-4-(biphenyll)methylaminopyridine derivatives.

Bioorganic & Medicinal Chemistry Letters (1994)

Robert H. Bradbury Martin P. Edwards Eric F. Fisher J. Alan Girdwood John S. Major

Structure–activity relationship

10.1016/s0960-894x(01)81136-7

Cite

Citations (1)

Design, Synthesis and Biological Activity of (20S,21S)‐7‐Cyclohexyl‐21‐fluorocamptothecin Carbamates as Potential Antitumor Agents

Chemistry & Biodiversity (2020)

Haijun Ma Baobao Chen Yuan Wang Chuanhao Wang Jianzhong Yao

Abstract (20 S ,21 S )‐7‐Cyclohexyl‐21‐fluorocamptothecin was discovered by a fluorine drug design strategy with potent antitumor activity and increased metabolic stability. In continuous efforts to find novel antitumor agents derived from natural product camptothecin, 20‐carbamates of the active compound (20 S ,21 S )‐7‐cyclohexyl‐21‐fluorocamptothecin have been designed and synthesized. Among them, one compound with the diethylamino group showed greater antiproliferative activity than the other 20‐carbamate derivatives. The following biological activity assays indicated that the above compound is a valuable lead compound with excellent Topo I inhibitory activity and solution stability.

Carbamate

Lead compound

Camptothecin

Metabolic stability

Natural product

10.1002/cbdv.202000068

Cite

Citations (4)