Novel trichloroindolizine derivatives via intramolecular acylation of a bis(chloroacyl)bipyridine

Sam, Najat; Elkadiri, S.; Bozec, Hubert Le; Toupet, Loı̈c; Daoudi, Maria; Bitit, Najib; Hadda, Taïbi Ben; Dixneuf, Pierre H.

doi:10.1039/b202616n

Cited by 5 publications

(3 citation statements)

References 9 publications

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“…We found that in addition to improving the yield of OPIC , the addition of gaseous chlorine to the reaction decreased the reaction time from 5h to 2h. The optimisation and mechanism of the formation of OPIC has been reported recently in more detail [ 20 ].…”

Section: Resultsmentioning

confidence: 99%

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Novel Cytotoxic Oxopyridoindolizines: iso-Propyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC)

Zunino¹,

Kotchevar

Waring

et al. 2002

Molecules

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A series of eight new alkyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC), analogues of camptothecin (CPT), were prepared in a one-pot reaction of 2,2'-bipyridine-3,3'-dicarboxylic acid (BPA) with a mixture of thionyl chloride/chlorine, followed by addition of the appropriate alcohol. This led to a mixture of OPIC compounds 3a-d, 4a-d and 3,3'-dialkoxycarbonyl-2,2'-bipyridines (BPE, 2a-d). The isopropyl OPIC 3c and its corresponding diastereoisomer 4c showed marked activity against three cancer cell lines compared to other analogs. These same diastereoisomers also displayed high cytotoxic activity against five leukemia cell lines, thus the presence of an isopropyl substituent on the carboxylic ester, as opposed to other alkyl substituents, appears to play a key role in the cytotoxic potency of this new class of compounds.

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Section: Resultsmentioning

confidence: 99%

“…for C 14 H 11 NO 3 Cl 3 : 360.63); IR (KBr) n cm -1 : 1750 (C=O, s), 1716 (C=O, s), 1609, 1580 (C=C, w), 1457 (C=N, m). The crystallographic structure of 4b has been reported [ 20 ].…”

Section: Methodsmentioning

confidence: 99%

Novel Cytotoxic Oxopyridoindolizines: iso-Propyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC)

Zunino¹,

Kotchevar

Waring

et al. 2002

Molecules

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“…The ligand C was prepared by a similar procedure as described in our previous work [18]. The 2,2 0 -bipyridine-3,3 0 -dicarboxylic acid was prepared from 1,10-phenanthroline by a literature procedure.…”

Section: Antitubercular Activitymentioning

confidence: 99%

Anti-tubercular Activity of Ruthenium (II) Complexes with Polypyridines

Hadda

Akkurt

Baba

et al. 2008

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of nine polypyridyl-ruthenium (II) complexes (N-ligands ¼ 2,2 0 -bipyridines; 2,2 0 -6 0 ,2 0 -terpyridines, di-alkyloxy-2, 2 0 -6,2-bipyridine-3,3 0 -di-carboxylates), were tested against Mycobacterium tuberculosis (MBT). The complex (11) showed remarkable activity against MBT as compared to other complexes, (1-10). The aquo ligand of complex (11), as opposed to other chloro and acetonitrile derivatives, appears to play a key role in the antitubercular potency of this new class of metal-based compounds.

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