Synthesis, in vitro Antiproliferative and Anti-HIV Activity of New Derivatives of 2-Piperazino-1,3-benzo[d]thiazoles

Abstract

A series of N- {2-oxo-2-[4-(1,3-benzothiazol-2-yl)piperazin-1-yl]}-(het)arenecarboxamides 4a -l, sulfonamide derivatives 8a -i as well as benzothiazole-containing N 1 -(2-oxoethyl)-N 1 -arylthioureas 9a -c have been synthesized. Compounds 4a -l and 9a were evaluated, in vitro, for their antiproliferative activity against a large panel of human tumor-derived cell lines. Compounds 4l and 9a were the most potent analogs in this series, showing remarkable effects on human splenic B-lymphoblastoid cells (WIL-2NS) and human acute B-lymphoblastic leukemia (CCRF-SB) cell lines (4l: CC 50 = 5.1 and 7.3 µ M, respectively), and compound 5 against CCRF-SB cell lines with CC 50 = 2.3 µ M. These compounds are leading candidates for further development. Compounds 6 -7a -i were screened as inhibitors against HIV-1 and HIV-2, and no activity has been witnessed.

Thiazole as an Indispensable Scaffold in Anti‐Leukemic Agents: A Semicentennial Review

“…The biological study of the synthesized 2‐piperazino‐1,3‐benzo[ d ]thiazoles derivative 100 demonstrating impressive effectiveness on human acute T‐lymphoblastic leukemia CCRF‐CEM and B‐lymphoblastic leukemia CCRF‐SB, and the CC 50 value for 102 in CCRF‐SB cell line is 7.3 μM and for compound 100 , CC 50 value is 2.3 μM. To sum up, the addition of a thiourea residue increased the activity of the derivatives of benzothiazoles when compared to other analogs [32] …”

“…To sum up, the addition of a thiourea residue increased the activity of the derivatives of benzothiazoles when compared to other analogs. [32] In the same year, an environment-friendly and operational route for the synthesis of The biological study of the library of fused benzothiazole derivatives revealed compound 107, which has a tert-butyl substitution at the para position, as the one having greater potency. For both cell lines, at 10 μM of 107 total cell death was observed.…”

Synthesis and Anticancer Evaluations of Novel Thiazole Derivatives Derived from 4-Phenylthiazol-2-amine

“…Great concern has been recently focused on the development of heterocyclic compound bearing 1,3-thiazole ring system, which has been identified as a central structural element of several biologically active natural products such as thiamine vitamin B, and pharmacologically active substances in a large number of drugs as antibacterial, 1,2 antifungal, 3,4 antiviral, [5][6][7] anti-inflammatory, 8,9 anticancer, [10][11][12][13][14] anti-HIV, [15][16][17] anti-oxidant 18,19 and analgesic drugs. 20,21 Both classical and non-classical synthetic methods approaches were used to synthesize thiazole derivatives.…”