5426-11-9Relevant articles and documents
Convenient synthesis, anticancer evaluation and QSAR studies of some thiazole tethered indenopyrazoles
Mor, Satbir,Nagoria, Savita,Kumar, Ashwani,Monga, Jitender,Lohan, Sandeep
, p. 1096 - 1114 (2016)
Abstract: A convenient one-pot synthesis of twelve new thiazole tethered indeno[1,2-c]pyrazol-4-ones (3a–3l) was carried out by three-component reaction between 1,3-diketones, thiosemicarbazide and α-bromoketones in high yields. Wolff-Kishner reduction of indeno[1,2-c]pyrazol-4-ones (3a–3l) led to the formation of corresponding indeno[1,2-c]pyrazoles (4a–4l) in moderate-to-good yields. The structures of all the synthesized indenopyrazoles were elucidated by IR, 1H NMR, 13C NMR and mass spectral techniques. In vitro cytotoxicity of thiazole tethered indenopyrazoles (3a–3l & 4a–4l) was evaluated against different human cancer cell lines, viz. human renal carcinoma (A498), human colorectal adenocarcinoma (HT29), human breast adenocarcinoma (MCF-7), human hepatocellular carcinoma (HepG2) and normal cell line, i.e., normal rat kidney epithelial (NRK). Among all the tested derivatives, 4a, 4d and 4h exhibited better activity against HT29 cancer cell line. The statistically significant QSAR models were developed for all the cancer cell lines using multiple linear regression analysis to understand the observed activity trend on structural basis. Graphical Abstract: [Figure not available: see fulltext.]
Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones
Mor, Satbir,Sindhu, Suchita
, p. 46 - 62 (2019/11/13)
We report a convenient and efficient synthesis of indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) by the reaction of a variety of 2-acyl-(1H)-indene-1,3(2H)-diones (1) and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles (2) in the presence of glacial acetic acid in good yields. The structure of the compounds thus prepared were confirmed by analytical and spectral (FT-IR, 1H NMR, 13C NMR, and HRMS) techniques. All the synthesized indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) were assayed for their in vitro Type II diabetes inhibitory activity by using Acarbose as standard drug and in vitro antimicrobial activity utilizing Streptomycin and Fluconazole as reference drugs. Among the synthesized derivatives, 4e (IC50 = 6.71 μg/mL) was found to be more potent against α-glucosidase enzyme as compared with the standard Acarbose (IC50 = 9.35 μg/mL) and 4i (IC50 = 11.90 μg/mL) exhibited good inhibitory activity against α-amylase enzyme as compared with the standard Acarbose (IC50 = 22.87 μg/mL). Also, all the titled compounds showed good antimicrobial activity. In addition, in vitro α-glucosidase and α-amylase inhibition were supported by docking studies performed on the derivatives 4e and 4o, respectively. [Figure not available: see fulltext.].
A method for C2 acylation of 1,3-indandiones
Larsen, Brian J.,Rosano, Robert J.,Ford-Hutchinson, Thomas A.,Reitz, Allen B.,Wrobel, Jay E.
, p. 2762 - 2768 (2018/04/30)
The 1,3-indandione scaffold is an important structural motif used in the preparation of a large number of industrial chemical and pharmaceutical compounds. However, few approaches allow for the direct C2 acylation on these building blocks. A method was developed using DMAP and EDCI, which is mild in reactivity, covers a diverse range of carboxylic acid acylating agents, is compatible with electron releasing and withdrawing substituents on the 1,3-indandione partner, and performs well in a polar aprotic solvent (for solubility reasons) This method cleanly afforded twenty five different products in yields of 32–96%.
