Synthesis and structure verification of an analogue of kuanoniamine A

Lyon, Michael A.; Lawrence, Simon E.; Williams, David J.; Jackson, Yvette A.

doi:10.1039/a809203f

Cited by 41 publications

(29 citation statements)

References 24 publications

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“…The molecular structure is approximately planar (Fig. 1), the thiazolopyridine ring system and the phenyl ring being slightly twisted by 9.685 (12) , which is comparable to the corresponding angles reported in 5-dimethylamino-2-phenyl-4,7-dioxobenzothiazole (Lyon et al, 1999) and 5-benzyl-2phenyl-4-tolylthiazole (Bart et al, 1978). The bond distances of S1-C7 and S1-C12 in (I) ( Table 1) are a little longer than those in other thiazolo derivatives (Kasim & Yamin, 2005;Cui et al, 2005).…”

Section: Commentsupporting

confidence: 77%

6-(Methylsulfanyl)-2-phenylthiazolo[5,4-b]pyridine

Wang

et al. 2007

Acta Cryst E

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Section: Commentsupporting

confidence: 77%

6-(Methylsulfanyl)-2-phenylthiazolo[5,4-b]pyridine

Wang

et al. 2007

Acta Cryst E

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“…Some of these derivatives may have anti-tuberculosis activity in vitro against various strains of Mycobacterium (Eswaran et al, 2010a(Eswaran et al, ,b, 2009. Others have been studied as antibacterial agents (Desai et al, 2014;Vlahov et al, 1990) and antimalarials (Vandekerckhove & D'hooghe, 2015;Lyon et al, 1999;Nayak et al, 2016;Hamama et al, 2018;Chavan et al, 2016). ISSN 2056-9890 In an attempt to find novel bioactive cytotoxic molecules, we have synthesized a series of quinoline-3-carbonitrile and 2-chloroquinoline derivatives by the reaction mechanism illustrated in Fig.…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline

et al. 2019

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A new quinoline-based hydrazone, C16H12ClN3, was synthesized by a condensation reaction of 2-chloro-3-formylquinoline with phenylhydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012 Å), and forms a dihedral angle of 8.46 (10)° with the phenyl ring. The molecule adopts an E configuration with respect to the central C=N bond. In the crystal, molecules are linked by a C—H...π-phenyl interaction, forming zigzag chains propagating along the [10\overline{3}] direction. The N—H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent molecule, so linking the chains via weak N—H...π interactions to form of a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (35.5%), C...H/H...C (33.7%), Cl...H/H...Cl (12.3%), N...H/H...N (9.5%) contacts.

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“…Compounds incorporating quinoline ring system exhibited various biological, 11,12 and pharmaceutical activities e.g. anti-tuberculosis, 13 antiplasmodial, 14 antibacterial, 15,16 antihistamine, 17 antifungal, 18 antimalarial, 19,20 anti-HIV, 21 anticancer, 22 anti-inammatory, 23,24 anti-hypertensive, 25 and antioxidant activities. 26 In addition, the use of quinolines as tyrokinase PDGF-RTK inhibitor, 27 inositol 5 0 -phosphatase (SH 2 ), 28 DNA gyrase B inhibitors as Mycobacterium tuberculosis, 29 and DNA topoisomerase inhibitors, 30 were reported.…”

Section: Introduction and Scopementioning

confidence: 99%