Design, Synthesis and Cytotoxic Evaluation of Novel Lupane Triterpenoid and Ursolic Acid Derived 2-Aminobenzamides

Abstract

Series of novel triterpenoid hybrids were designed and synthesized by introducing 2-aminobenzamide moiety at C28 position of triterpenoid derivatives. Thirteen new conjugates were thus successfully prepared and evaluated as cytotoxic agents, revealing an interesting anticancer activity in KB and HepG2 cancer cell lines.

Design and Synthesis of New 2-Aminobenzamide Derivatives Containing Benzothiazole and Phenylamine Moiety and Their Cytotoxicity

“…The reaction was best performed using BOP as a carboxylic group activating agent. 15 Analogously, four 2-aminobenzamide derivatives containing phenylamine moiety (8a-b and 10a-b) were also synthesized, starting from compounds 6a-b via the amide intermediate 7a-b and 9a-b (Figure 4). The structures of the products were confirmed by analysis of spectral data such as 1 H NMR, 13 C NMR, IR, and MS (Supplemental Figures S32-S46).…”

“…On the other hand, 2-aminobenzamide are zinc binding groups in histone deacetylase structure (HDAC). 15 Several typical 2-aminobenzamide derivatives of this class such as chidamide (CS055), entinostat (MS-275), and mocetinostat (MGCD0103) (Figure 2) have been synthesized. Among these, CS055 has been approved by the FDA in 2015 to treat peripheral T-cell lymphoma 16 ; MGCD0103 17 and MS-275 18 are currently undergoing in human clinical trials for treatment of some types of cancer.…”

“…Among these, CS055 has been approved by the FDA in 2015 to treat peripheral T-cell lymphoma 16 ; MGCD0103 17 and MS-275 18 are currently undergoing in human clinical trials for treatment of some types of cancer. 15,19 From their superior biological activity, 2-aminobenzamide derivatives were designed and synthesized, which promise as anti-cancer drugs. 19,20 After considering the biological activity of benzothiazole and 2-aminobenzamide, 12 novel benzothiazole hybrids were created by the combination of benzothiazole and 1,2-diaminobenzene to form novel 2-aminobenzamide derivatives bearing benzothiazole…”

“…Among these, CS055 has been approved by the FDA in 2015 to treat peripheral T-cell lymphoma 16 ; MGCD0103 17 and MS-275 18 are currently undergoing in human clinical trials for treatment of some types of cancer. 15,19 From their superior biological activity, 2-aminobenzamide derivatives were designed and synthesized, which promise as anti-cancer drugs. 19,20…”