title: New 1-(3-nitrophenyl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines: synthesis and computational study.
abstract: Triazole derivatives constitute an important group of heterocyclic compounds have have been the subject of extensive study in the recent past. These compounds have shown a wide range of biological and pharmacological activities. In this work, new fused tricyclic 1-(3-nitrophenyl)-5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]-benzodiazepines have been synthesized by the thermal cyclization of N'-(2,3-dihydro-1H-1,5-benzodiazepin-4-yl)-3-nitrobenzohydrazides. After screening ethanol, toluene and 1-butanol as solvents, butanol-1 was found to be the best choice for the cyclization reaction in order to obtain the highest yields of tricyclic derivatives. The chemical structures of the synthesized compounds were elucidated by the analysis of their IR, 1H- and 13C-NMR spectral data. For tentative rationalization of the reaction processes, the global and local reactivity indices of certain compounds, taking part in the reaction pathway, were assessed by means of quantum mechanical calculations using the conceptual density functional theory (DFT) approach. This work could be useful for the synthesis of new heterocyclic compounds bearing a fused triazole ring.
authors.affiliation: Institute of Biochemistry, Vilnius University, Mokslininku 12, Vilnius LT-08662, Lithuania. lidija.kosychova@bchi.vu.lt.|Department of Technological Processes, Klaipeda University, H. Manto 84, Klaipeda LT-91001, Lithuania. lidija.kosychova@bchi.vu.lt.
authors.forename: Lidija
authors.initials: L
authors.lastname: Kosychova
authors.affiliation: Royal Institute of Technology, Department of Chemistry, Teknikringen 36, Stockholm S-10044, Sweden. antanas.karalius@gmail.com.
authors.forename: Antanas
authors.initials: A
authors.lastname: Karalius
authors.affiliation: Institute of Biochemistry, Vilnius University, Mokslininku 12, Vilnius LT-08662, Lithuania. zita.staniulyte@bchi.vu.lt.
authors.forename: Zita
authors.initials: Z
authors.lastname: Staniulytė
authors.affiliation: Institute of Biochemistry, Vilnius University, Mokslininku 12, Vilnius LT-08662, Lithuania. romualdas.sirutkaitis@bchi.vu.lt.
authors.forename: Romualdas Aleksas
authors.initials: RA
authors.lastname: Sirutkaitis
authors.affiliation: Institute of Biochemistry, Vilnius University, Mokslininku 12, Vilnius LT-08662, Lithuania. algirdas.palaima@bchi.vu.lt.
authors.forename: Algirdas
authors.initials: A
authors.lastname: Palaima
authors.affiliation: Institute of Biochemistry, Vilnius University, Mokslininku 12, Vilnius LT-08662, Lithuania. audrius.laurynenas@gmail.com.
authors.forename: Audrius
authors.initials: A
authors.lastname: Laurynėnas
authors.affiliation: Institute of Biochemistry, Vilnius University, Mokslininku 12, Vilnius LT-08662, Lithuania.
authors.forename: Žilvinas
authors.initials: Ž
authors.lastname: Anusevičius
mesh_terms: D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry; D019295:Computational Biology / Q000379:methods; D003500:Cyclization; D055595:Mechanical Phenomena; D008956:Models, Chemical; D015394:Molecular Structure; D011789:Quantum Theory
chemical_list: D001569:Benzodiazepines
references.citation: Proc Natl Acad Sci U S A. 1986 Nov;83(22):8440-1
references.pmid: 16578791
references.citation: Cancer Treat Rev. 2004 Jun;30(4):325-32
references.pmid: 15145507
references.citation: Org Biomol Chem. 2011 Oct 21;9(20):7168-75
references.pmid: 21842104
references.citation: Eur J Med Chem. 2012 Aug;54:87-94
references.pmid: 22621841
references.citation: Chem Rev. 2003 May;103(5):1793-873
references.pmid: 12744694
references.citation: Eur J Med Chem. 2004 Jun;39(6):535-45
references.pmid: 15183912
references.citation: Molecules. 2011 Jan 28;16(2):1297-309
references.pmid: 21278680
references.citation: Eur J Med Chem. 2006 Apr;41(4):531-8
references.pmid: 16529848
references.citation: Farmaco. 2004 Oct;59(10):775-83
references.pmid: 15474054
references.citation: Bioorg Med Chem Lett. 2001 Jul 9;11(13):1703-7
references.pmid: 11425542
references.citation: Eur J Med Chem. 2009 Dec;44(12):5066-70
references.pmid: 19822384
references.citation: J Org Chem. 2008 Jun 20;73(12):4615-24
references.pmid: 18484771
references.citation: Farmaco. 2004 Apr;59(4):255-9
references.pmid: 15081342
references.citation: Chem Asian J. 2014 Jan;9(1):166-78
references.pmid: 24124178
references.citation: Curr Top Med Chem. 2002 Aug;2(8):903-13
references.pmid: 12171579
references.citation: Bioorg Med Chem. 2007 Feb 15;15(4):1808-14
references.pmid: 17166724
references.citation: J Med Chem. 1979 Nov;22(11):1390-8
references.pmid: 42799