Use of 2-aminoprop-1-ene-1,1,3-tricarbonitrile for the synthesis of tetrahydronaphthalene, hexahydroisoquinoline and hexahydrocinnoline derivatives with potential antitumor activities
dc.Affiliation | October University for modern sciences and Arts (MSA) | |
dc.contributor.author | Mohareb R. | |
dc.contributor.author | Moustafa H. | |
dc.contributor.other | October University for Modern Sciences and Arts | |
dc.contributor.other | El Wahaat Road | |
dc.contributor.other | October City | |
dc.contributor.other | Egypt; Chemistry Department | |
dc.contributor.other | Faculty of Science | |
dc.contributor.other | Cairo University | |
dc.contributor.other | Giza | |
dc.contributor.other | Egypt; Applied Medical Sciences | |
dc.contributor.other | Department Community College in Quaryat | |
dc.contributor.other | Al Jouf University | |
dc.contributor.other | Al Jouf | |
dc.contributor.other | Saudi Arabia | |
dc.date.accessioned | 2020-01-25T19:58:31Z | |
dc.date.available | 2020-01-25T19:58:31Z | |
dc.date.issued | 2011 | |
dc.description | Scopus | |
dc.description.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. | en_US |
dc.description.uri | https://www.scimagojr.com/journalsearch.php?q=19398&tip=sid&clean=0 | |
dc.identifier.doi | https://doi.org/10.2478/v10007-011-0001-y | |
dc.identifier.doi | PubMed ID 21406343 | |
dc.identifier.issn | 13300075 | |
dc.identifier.other | https://doi.org/10.2478/v10007-011-0001-y | |
dc.identifier.other | PubMed ID 21406343 | |
dc.identifier.uri | https://t.ly/r8G1W | |
dc.language.iso | English | en_US |
dc.relation.ispartofseries | Acta Pharmaceutica | |
dc.relation.ispartofseries | 61 | |
dc.subject | antitumor activity | en_US |
dc.subject | hexahydrocinnoline | en_US |
dc.subject | hexahydroisoquinoline | en_US |
dc.subject | tetrahydronaphthalene | en_US |
dc.subject | 2 (amino(3 oxo 2 (1,4 ditolylamino) 2,3,5,6,7,8 hexahydrocinnolin 4 yl)methylene)malononitrile | en_US |
dc.subject | 2 [amino(2,3 diamino 1 phenyl 1,2,5,6,7,8 hexahydroisoquinolin 4 yl)methylene]malononitrile | en_US |
dc.subject | 2 [amino[2,3,5,6,7,8 hexahydro 3 imino 2 (1,4 ditolylcinnoline) 4 yl]methylene]malononitrile | en_US |
dc.subject | 2 amino 3 (2 benzylidene 6 bromocyclohexylidene)prop 1 ene 1,1,3 tricarbonitrile | en_US |
dc.subject | 2 amino 3 (2 benzylidenecyclohexylidene)prop 1 ene 1,1,3 tricarbonitrile | en_US |
dc.subject | 3 amino 2 cyano 4 [2 (1,4 ditolyl hydrazono) cyclohexylidene]prop 1 ene 1,1,3 tricarbonitrile | en_US |
dc.subject | 3 amino 3 (3,5 diamino 4h pyrazol 4 ylidene) 2 cyclohexylidene propanonitrile | en_US |
dc.subject | 3 amino 3 [3 amino 5 imino 1 phenyl 1h pyrazol 4 (5h) ylidene] 2 cyclohexylidenepropanonitrile | en_US |
dc.subject | 3 amino 4 (1 amino 2,2 dicyanovinyl) 1 phenyl 5,6,7,8 tetrahydro 1 phenylnaphthalene 2 carbonitrile | en_US |
dc.subject | 4 [2 benzylidenecyclohexylidene)(cyano)methyl] 1,2,3,6 tetrahydro 6 imino 1 phenyl 2 thioxopyrimidine 5 carbonitrile | en_US |
dc.subject | antineoplastic agent | en_US |
dc.subject | cyanide | en_US |
dc.subject | cyclohexanone | en_US |
dc.subject | ethyl 3 amino 4 (1 amino 2,2 dicyanovinyl) 5,6,7,8 tetrahydro 1 phenylnaphthalene 2 carboxylate | en_US |
dc.subject | isoquinoline derivative | en_US |
dc.subject | tetralin derivative | en_US |
dc.subject | unclassified drug | en_US |
dc.subject | antineoplastic activity | en_US |
dc.subject | article | en_US |
dc.subject | brain cancer | en_US |
dc.subject | breast adenocarcinoma | en_US |
dc.subject | cancer cell culture | en_US |
dc.subject | controlled study | en_US |
dc.subject | drug effect | en_US |
dc.subject | drug synthesis | en_US |
dc.subject | human | en_US |
dc.subject | human cell | en_US |
dc.subject | in vitro study | en_US |
dc.subject | lung non small cell cancer | en_US |
dc.subject | Antineoplastic Agents | en_US |
dc.subject | Cell Line, Tumor | en_US |
dc.subject | Drug Screening Assays, Antitumor | en_US |
dc.subject | Heterocyclic Compounds, 2-Ring | en_US |
dc.subject | Humans | en_US |
dc.subject | Isoquinolines | en_US |
dc.subject | Neoplasms | en_US |
dc.subject | Tetrahydronaphthalenes | en_US |
dc.title | Use of 2-aminoprop-1-ene-1,1,3-tricarbonitrile for the synthesis of tetrahydronaphthalene, hexahydroisoquinoline and hexahydrocinnoline derivatives with potential antitumor activities | en_US |
dc.type | Article | en_US |
dcterms.isReferencedBy | Bolognese, A., Correale, G., Manfra, M., Lavecchia, A., Novellino, E., Pepe, S., Antitumor agents. 5. Synthesis, structure - activity relationships, and biological evaluation of dimethyl-5H-pyridophenoxazin-5-ones, tetrahydro-5H-benzopyridophenoxazin-5-ones, and 5H-benzopyridophenoxazin-5-ones with potent antiproliferative activity (2006) Journal of Medicinal Chemistry, 49 (17), pp. 5110-5118. , DOI 10.1021/jm050745l; Heimer, G., Rivlin-Etzion, M., Bar-Gad, I., Goldberg, J.A., Haber, S.N., Bergman, H., Dopamine replacement therapy does not restore the full spectrum of normal pallidal activity in the 1-methyl-4-phenyl-1,2,3,6-tetra-hydropyridine primate model of Parkinsonism (2006) Journal of Neuroscience, 26 (31), pp. 8101-8114. , http://www.jneurosci.org/cgi/reprint/26/31/8101, DOI 10.1523/JNEUROSCI.5140-05.2006; Powers, R., Copeland, J.C., Germer, K., Mercier, K.A., Ramanatlian, V., Revesz, P., Comparison of protein active site structures for functional annotation of proteins and drug design (2006) Proteins: Structure, Function and Genetics, 65 (1), pp. 124-135. , DOI 10.1002/prot.21092; Wing, L.K., Behanna, H.A., Van Eldik, L.J., Watterson, D.M., Ranaivo, H.R., De novo and molecular target-independent discovery of orally bioavailable lead compounds for neurological disorders (2006) Current Alzheimer Research, 3 (3), pp. 205-214. , http://docstore.ingenta.com/cgi-bin/ds_deliver/1/u/d/ISIS/30194081.1/ben/ car/2006/00000003/00000003/art00008/1D1CCD51B83CFEDF1151479621CF342172FEF0A932. pdf?link=http://www.ingentaconnect.com/error/delivery&format=pdf, DOI 10.2174/156720506777632844; Xin, Z., Serby, M.D., Zhao, H., Kosogof, C., Szczepankiewicz, B.G., Liu, M., Liu, B., Liu, G., Discovery and pharmacological evaluation of growth hormone secretagogue receptor antagonists (2006) Journal of Medicinal Chemistry, 49 (15), pp. 4459-4469. , DOI 10.1021/jm060461g; Sadzeviciene, R., Zekonis, J., Zekonis, G., Paipaliene, P., Oxidative functions of neutrophils in perioponditis patients with type 1 diabetes mellitus (2006) Medicina (Kaunas), 42, pp. 479-483; Romagnoli, R., Baraldi, P.G., Remusat, V., Carrion, M.D., Lopez Cara, C., Preti, D., Fruttarolo, F., Hamel, E., Synthesis and biological evaluation of 2-(3?,4?,5?- trimethoxybenzoyl)-3-amino 5-aryl thiophenes as a new class of tubulin inhibitors (2006) Journal of Medicinal Chemistry, 49 (21), pp. 6425-6428. , DOI 10.1021/jm060804a; Zhao, H., Serby, M.D., Xin, Z., Szczepankiewicz, B.G., Liu, M., Kosogof, C., Liu, B., Liu, G., Discovery of potent, highly selective, and orally bioavailable pyridine carboxamide c-Jun NH2-terminal kinase inhibitors (2006) Journal of Medicinal Chemistry, 49 (15), pp. 4455-4458. , DOI 10.1021/jm060465l; Arif, J.M., Kunhi, M., Bekhit, A.A., Subramanian, M.P., Al-Hussein, K., Aboul-Enein, H.Y., Al-Khodairy, F.M., Evaluation of apoptosis-induction by newly synthesized phthalazine derivatives in breast cancer cell lines (2006) Asian Pac. J. Cancer Prev., 7, pp. 249-252. , DOI: 10.1093/aje/ kwj264; Fareh, J., Touyz, R.M., Schiffrin, E.L., Thibault, G., Altered cardiac endothelin receptors and protein kinase C in deoxycorticosterone-salt hypertensive rats (2000) Journal of Molecular and Cellular Cardiology, 32 (4), pp. 665-676. , DOI 10.1006/jmcc.2000.1110; Junek, H., Thierrichter, B., Wibmer, P., Synthesis with nitriles, Comparative reactivity studies of the new codimers from malononitrile and ethyl cyanoacetate with carbonyl compounds (1979) Monatsh. Chem., 110, pp. 483-492; Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J.T., Boyd, M.R., New colorimetric cytotoxicity assay for anticancer-drug screening (1990) Journal of the National Cancer Institute, 82 (13), pp. 1107-1112; Monks, A., Scudiero, D., Skehan, P., Shoemaker, R., Paul, K., Vistica, D., Hose, C., Boyd, J.M., Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines (1991) J. Natl. Cancer Inst., 83, pp. 757-776. , DOI: 10.1093/jnci/83.11.757; Mohareb, R.M., Ghabrial, S.S., Wardakhan, W.W., The uses of 4-aryl-3-thiosemicarbazides in heterocyclic syn thesis: Synthesis of coumarin, pyrazole, thiazole and thiophene derivatives (1998) Phosphorus Sulfur, 134, pp. 119-134. , DOI: 10.1080/10426509808545457; Mohareb, R.M., Manhi, F.M., Reaction of ethyl 2-diazo-4,5,6,7-tetrahydrobenzo[b]thiophene-3- carboxylate with 3-iminobutyronitrile: Synthesis of pyridazines, thiophenes, and their fused derivatives (2000) Heteroat. Chem., 11, pp. 403-412. , DOI: 10.1002/1098-1071; Sandstrom, J.T., Measurement and calculation of [sup.13]C and [sup.15]N NMR chemical-shift tensors of a push-pull ethylene (1983) Top. Stereochem., 14, pp. 83-181. , DOI: 10.1002/ 9780470147238.ch2 | |
dcterms.source | Scopus |
Files
Original bundle
1 - 2 of 2
Loading...
- Name:
- avatar_scholar_256.png
- Size:
- 6.31 KB
- Format:
- Portable Network Graphics
- Description:
Loading...
- Name:
- [18469558 - Acta Pharmaceutica] Use of 2-aminoprop-1-ene-1,1,3-tricarbonitrile for the synthesis of tetrahydronaphthalene, hexahydroisoquinoline and hexahydrocinnoline derivatives with potential antitumor activities.pdf
- Size:
- 96.74 KB
- Format:
- Adobe Portable Document Format
- Description: