In the light of these findings, 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazone derivatives were synthesized in order to obtain more potent and less toxic compounds. The structures of the ABSTRACT: A series of 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazones 3a-g were synthesized to investigate the chemotherapeutic activities. The structures of 3a-g were confirmed by the spectral data (IR, 1 H NMR, 13 C NMR-APT, 13 C NMR-DEPT, HSQC, HMBC) and elemental analysis. Anticancer activities of the compounds were evaluated using cell kinetic parameters on HeLa cells derived from human cervix carcinoma. The preliminary screening results indicated that alkyl substituted compounds 3a, 3b and 3d were more effective in mitosis phase when compared to the synthesis phase. 3a-g were tested against some DNA and RNA viruses in CRFK, HeLa, HEL, MDCK and Vero cells. None of the compounds was active against any of the RNA or DNA viruses at 100 μM. All compounds were also evaluated for antimicrobial activity against selected strains. Methyl substituted 3a and allyl substituted 3c were found to be active against S. aureus and C. albicans.
The title compound, C14H9ClN2OS, crystallizes with two unique molecules, A and B, in the asymmetric unit. The five-membered rings of the benzothiazole groups in both molecules adopt an envelope conformation [puckering parameters: q
2 = 0.242 (1) Å and ϕ2 = 217.5 (4)° for A, and q
2 = 0.234 (1) Å and ϕ2 = 37.7 (4)° for B]. The five-membered rings of the indolinone groups in both molecules are also not planar, with a twisted conformation [puckering parameters are q
2 = 0.112 (2) Å and ϕ2 = 126.3 (8)° for A, and q
2 = 0.108 (2) Å and ϕ2 = 306.4 (9)° for B]. In the crystal structure, there are intermolecular N—H⋯O, N—H⋯S and C—H⋯O hydrogen-bonding interactions, forming the layers propagating normal to c.
In this study, 5-chloro-3H-spiro-[1,3-benzothiazole-2,3 0 -indole]-2 0 (1 0 H)-one derivatives 3a-l were synthesized by the reaction of 1H-indole-2,3-diones 1a-l with 2-amino-4-chlorothiophenol 2 in ethanol. 3a-l were tested for their abilities to inhibit lipid peroxidation (LP), scavenge DPPH and ABTS þ radicals, and to reduce Fe 3þ to Fe 2þ . Most of the tested compounds exhibited potent scavenging activities against ABTS þ radical, reducing powers and strong inhibitory capacity on LP. 3 a, 3 d, 3e, 3h, 3j and 3 k chosen as prototypes were evaluated in the National Cancer Institute's in vitro primary anticancer assay. The greatest growth inhibitions were observed against a non-small cell lung cancer cell line HOP-92 for R 1 -fluoro substituted 3 d and a renal cancer cell line RXF-393 for R-chloro substituted 3 e in the primary screen.
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