112253-72-2Relevant academic research and scientific papers
Novel substituted triazolo benzodiazepine scaffolds to explore chemical space
Abeykoon, Gayan A.,Sahn, James J.,Martin, Stephen F.
, (2021/02/16)
Efficient and concise routes to sets of novel triazolo-1,4-benzodiazepine scaffolds that are suitably functionalized for diversification at three positions to explore three-dimensional space with different substituents are described. One approach to these scaffolds features a simplified multicomponent assembly process to give an intermediate azido alkyne that undergoes a facile Huisgen dipolar cycloaddition. The triazolo-1,4-benzodiazepines thus produced may be endowed with aryl halide, secondary amino, alcohol, aldehyde or carboxylic acid groups as functional handles for orthogonal derivatization reactions. Modification of this approach enabled the facile synthesis of the related triazolo-1,4-benzodiazepin-6-ones, also bearing three functional handles. These convenient protocols were used to prepare multi-gram quantities of benzodiazepine analogs as precursors for generating compound libraries for screening campaigns.
Reactions of 1-Arylbenziodoxolones with Azide Anion: Experimental and Computational Study of Substituent Effects
Yusubov, Mekhman S.,Soldatova, Natalia S.,Postnikov, Pavel S.,Valiev, Rashid R.,Svitich, Dmitry Y.,Yusubova, Roza Y.,Yoshimura, Akira,Wirth, Thomas,Zhdankin, Viktor V.
, p. 640 - 647 (2018/02/14)
New substituted 1-arylbenziodoxolones were prepared and their reactivity with azide anion as a nucleophile was investigated. It was found that independent of the presence of substituents, all reactions of 1-arylbenziodoxolones proceed as nucleophilic substitution of the iodonium leaving group in the electron-deficient benziodoxolone benzene ring. The presence of bulky substituents in the ortho position of the aryl ring slows the reaction down, while the presence of a moderately electron-withdrawing bromine substituent in para position to the iodine atom in the benziodoxolone ring moderately increases the rate of substitution. The presence of a strongly electron-withdrawing nitro group in the para position to the iodine atom in the benziodoxolone ring dramatically increases the rate of substitution. These observations are in agreement with the electronic requirements for internal nucleophilic substitution in the benziodoxole ring. A quantum-chemical computational study of the possible reaction paths is in agreement with the observed effects of substituents on the reactivity of arylbenziodoxolones in this reaction.
Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids
Dzhons, Daria Yu.,Budruev, Andrei V.
supporting information, p. 874 - 881 (2016/07/06)
The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation and photolysis of 2-azidobenzoate anions.
Click chemistry based rapid one-pot synthesis and evaluation for protease inhibition of new tetracyclic triazole fused benzodiazepine derivatives
Mohapatra, Debendra K.,Maity, Pradip K.,Shabab,Khan
scheme or table, p. 5241 - 5245 (2010/03/24)
We describe herein a one-pot synthesis of novel tetracyclic scaffolds that incorporate a fusion of a proline, 1,2,3-triazole ring with [1,4]-benzodiazepin-8(4H)-one ring systems following click chemistry. The expected peptide bond formation followed by in
Intramolecular 1,3-Dipolar Cycloadditions. Part 1. A Facile Synthesis of Benzimidazo- and Quinazolinotriazolobenzodiazepines
Mohiuddin, Ghulam,Reddy, Padala Satyanarayana,Ahmed, Khalil,Ratnam, Chengalvala Venkata
, p. 1839 - 1868 (2007/10/02)
The synthesis of hitherto unknown 9H-benzimidazotriazolobenzodiazepines (4, 11a-e and 12a-c) and 9H-quinazolinotriazolobenzodiazepin-11-ones (5 and 18a-g) is reported. 2-(2-Azidoaryl)benzimidazoles (6 and 10a-h) and 2-(2-azidoaryl)quinazolin-4(3H)-ones (7 and 17a-g) react with propargyl bromide to give non-isolable intermediates which undergo an intramolecular 1,3-dipolar cycloaddition to the title compounds.
