Use of 2-aminoprop-1-ene-1,1,3-tricarbonitrile for the synthesis of tetrahydronaphthalene, hexahydroisoquinoline and hexahydrocinnoline derivatives with potential antitumor activities

Mohareb R.; Moustafa H.

MSAR Home
→
MSA University Academic Research
→
Research Papers, Articles and Books Chapters.
→
Faculty Of Pharmacy Research Paper
→
View Item

Use of 2-aminoprop-1-ene-1,1,3-tricarbonitrile for the synthesis of tetrahydronaphthalene, hexahydroisoquinoline and hexahydrocinnoline derivatives with potential antitumor activities

Mohareb R.; Moustafa H.

Full Text link: https://t.ly/r8G1W

Date issued: 2011

Scientific Journal Rankings: Click Here

Doi: https://doi.org/10.2478/v10007-011-0001-y PubMed ID 21406343

Series Info: Acta Pharmaceutica
61

Type: Article

Keywords: antitumor activity , hexahydrocinnoline , hexahydroisoquinoline , tetrahydronaphthalene , 2 (amino(3 oxo 2 (1,4 ditolylamino) 2,3,5,6,7,8 hexahydrocinnolin 4 yl)methylene)malononitrile , 2 [amino(2,3 diamino 1 phenyl 1,2,5,6,7,8 hexahydroisoquinolin 4 yl)methylene]malononitrile , 2 [amino[2,3,5,6,7,8 hexahydro 3 imino 2 (1,4 ditolylcinnoline) 4 yl]methylene]malononitrile , 2 amino 3 (2 benzylidene 6 bromocyclohexylidene)prop 1 ene 1,1,3 tricarbonitrile , 2 amino 3 (2 benzylidenecyclohexylidene)prop 1 ene 1,1,3 tricarbonitrile , 3 amino 2 cyano 4 [2 (1,4 ditolyl hydrazono) cyclohexylidene]prop 1 ene 1,1,3 tricarbonitrile , 3 amino 3 (3,5 diamino 4h pyrazol 4 ylidene) 2 cyclohexylidene propanonitrile , 3 amino 3 [3 amino 5 imino 1 phenyl 1h pyrazol 4 (5h) ylidene] 2 cyclohexylidenepropanonitrile , 3 amino 4 (1 amino 2,2 dicyanovinyl) 1 phenyl 5,6,7,8 tetrahydro 1 phenylnaphthalene 2 carbonitrile , 4 [2 benzylidenecyclohexylidene)(cyano)methyl] 1,2,3,6 tetrahydro 6 imino 1 phenyl 2 thioxopyrimidine 5 carbonitrile , antineoplastic agent , cyanide , cyclohexanone , ethyl 3 amino 4 (1 amino 2,2 dicyanovinyl) 5,6,7,8 tetrahydro 1 phenylnaphthalene 2 carboxylate , isoquinoline derivative , tetralin derivative , unclassified drug , antineoplastic activity , article , brain cancer , breast adenocarcinoma , cancer cell culture , controlled study , drug effect , drug synthesis , human , human cell , in vitro study , lung non small cell cancer , Antineoplastic Agents , Cell Line, Tumor , Drug Screening Assays, Antitumor , Heterocyclic Compounds, 2-Ring , Humans , Isoquinolines , Neoplasms , Tetrahydronaphthalenes

Abstract:

The aim of the work was to synthesize heterocyclic compounds from 2-aminoprop-1-ene-1,1,3-tricarbonitrile and to study their antitumor activities. The title reagent reacted with cyclohexanone to give the ethylidene derivative 2. The reactivity of the latter product towards different chemical reagents was studied to give tetrahydronaphthalene, hexahydroisoquinoline and hexahydrocinnoline derivatives. The newly synthesized products were screened as antitumor agents on the in vitro growth of three human tumor cell lines representing different tumor types, namely, breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268). It was found that some of these compounds showed inhibitory effects on the three cell lines, indicating their potential use in the development of oncology products.