2-Ethoxycarbonylimino-2<i>H</i>-1,2,4-thiadiazolo[2,3-<i>a</i>]pyridine monohydrate

Leban, I.

doi:10.1107/s0567740876005979

Cited by 12 publications

(3 citation statements)

References 4 publications

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“…The already published compounds containing [1,2,4]thiadiazolo[2,3-a]pyridine, which were produced by oxidative cyclization reaction of N-pyridyl-thioureas, are neither a benzamide derivative nor similar to our ligands O1, O2, and O3. 41,42 Although 2,5-disubstituted oxazoles 43 and furoxan 44 have been reported to be produced by oxidative cyclization using the copper(II) ion as an oxidant, contrary to our products, they are not able to react as ligands and cannot connect to copper ions to form complexes.…”

Section: Spectroscopic Studiesmentioning

confidence: 80%

Synthesis, crystal structure, and cytotoxic activity of novel cyclic systems in [1,2,4]thiadiazolo[2,3-a]pyridine benzamide derivatives and their copper(ii) complexes

et al. 2014

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Three N-(pyridine-2-ylcarbamothioyl)benzamide derivatives were synthesized by the reaction of potassium thiocyanate, benzoyl chloride, and 2-amino pyridine derivatives in one pot. The obtained derivatives were oxidized using copper(ii) chloride. During the oxidation, two hydrogen atoms were removed, cyclization of the derivatives occurred, and finally, three new N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2-ylidene)benzamide derivatives were produced. Coordination of these three new derivative ligands to the copper(II) ion resulted in the formation of three new complexes: dichlorobis(N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2-ylidene)benzamide)copper(II), dichlorobis(N-(7-methyl-2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2ylidene)benzamide)copper(II), and dichlorobis(N-(5-methyl-2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2-ylidene)benzamide)copper(II). All the synthesized products were characterized by IR, (1)H NMR, and (13)C NMR spectroscopies. Crystal structures of the obtained N-(pyridine-2-ylcarbamothioyl)benzamide derivatives, N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2-ylidene)benzamide derivatives, and complexes were determined using X-ray single-crystal diffraction; the positions of atoms, bond lengths, bond angles, and dihedral angles were also determined. In all complexes, the coordination of two large monodentate ligands and two chloride anions to the copper(ii) ion resulted in the formation of a stable planar geometry around the central ion. Three N-(pyridine-2-ylcarbamothioyl)benzamide derivatives, three N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2-ylidene)benzamide derivatives, and three complexes were evaluated for their cytotoxicity against five human cancer cell lines (breast cancer cell line MDA-MB-231, neuroblastoma cell line SK-N-MC, prostate adenocarcinoma cell line LNCap, nasopharyngeal epidermoid carcinoma cell line KB, and liver cancer cell line HEPG-2) using an in vitro analysis. The N-(pyridine-2-ylcarbamothioyl)benzamide derivatives showed no cytotoxic activity, whereas the N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2-ylidene)benzamide derivatives and their complexes showed significant cytotoxicity, especially against MDA-MB-231 and LNCap cell lines. The complexes demonstrated smaller IC50 values than N-(2H-[1,2,4]thiadiazolo[2,3-a]pyridine-2-ylidene)benzamide derivatives.

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Section: Spectroscopic Studiesmentioning

confidence: 80%

Synthesis, crystal structure, and cytotoxic activity of novel cyclic systems in [1,2,4]thiadiazolo[2,3-a]pyridine benzamide derivatives and their copper(ii) complexes

et al. 2014

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“…The relative ordering of the electron-attractive force of the O=Y-R' moieties is: O Leban (1976); (5) Gieren & Dederer (1978); (6) Sletten & Velsvik (1973); (7) Hordvik, Sletten & Sletten (1969); (8) Bardi, Piazzesi & Busetti (1979); (9) Hamilton & LaPlaca (1964); (10) Mellor & Nyburg (1971b); (11) Hordvik & Kjoge (1966); (12) Schmid et aL (1975); (13 Table 7. Symbols 4, 5 and 6 stand for four-, five-or six-membered B rings (Table 7), while 0 represents structures in which there is no ring B.…”

Section: Discussionmentioning

confidence: 99%

Structure of 2-benzoylimino-3-methyl-1,3-thiazolidine: a comparison of intramolecular X–S...O = Y interactions

Kàlmán¹,

Parkanyi²

1980

Acta Crystallogr Sect B

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“…The C(7)--N(2) bond has a length of 1.300 (3)A which places it mid-range of imino bond distances observed in similar structures where the C atom is part of a five-membered ring; e.g., the related thiadiazolo and dithiadiazolo compounds display imino bond lengths in the range 1.24-1.32 A (Sato, Kinoshita, Hata & Tamura, 1977, 1980Leban, 1976;Gieren & Dederer, 1978). Constraints imposed by the isothiazole ring in (II) yield bond angles of 107.8 (2), 125.4 (2) and 126.8 (2) ° about C(7) ( Table 2).…”

Section: C13hi2n2osmentioning

confidence: 99%