Molecules 2002, 7(8), 628-640; doi:10.3390/70800628
Article

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

1, 2, 3, 4, 4, 5, 5, 5 and 4,5,* email
Received: 16 May 2002; in revised form: 5 August 2002 / Accepted: 5 August 2002 / Published: 31 August 2002
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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.
Keywords: Oxopyridopyndolizine carboxylate (OPIC); Cycloacylation; Camptothecin; Cancer; Chlorination; N-ligands
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MDPI and ACS Style

Zunino, F.; Kotchevar, A.T.; Waring, M.; Daoudi, M.; Larbi, N.B.; Mimouni, M.; Sam, N.; Zahidi, A.; Ben-Hadda, T. Novel Cytotoxic Oxopyridoindolizines: iso-Propyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC). Molecules 2002, 7, 628-640.

AMA Style

Zunino F, Kotchevar AT, Waring M, Daoudi M, Larbi NB, Mimouni M, Sam N, Zahidi A, Ben-Hadda T. Novel Cytotoxic Oxopyridoindolizines: iso-Propyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC). Molecules. 2002; 7(8):628-640.

Chicago/Turabian Style

Zunino, Franco; Kotchevar, Ann T.; Waring, Michael; Daoudi, Maria; Larbi, Najib B.; Mimouni, Mostafa; Sam, Najat; Zahidi, Assou; Ben-Hadda, Taibi. 2002. "Novel Cytotoxic Oxopyridoindolizines: iso-Propyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC)." Molecules 7, no. 8: 628-640.


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