25173-37-9Relevant articles and documents
Acid activated montmorillonite K-10 mediated intramolecular acylation: Simple and convenient synthesis of 4-chromanones
Begum, Ayisha F.,Balasubramanian, Kalpattu K.,Shanmugasundaram, Bhagavathy
supporting information, (2021/09/13)
3-Aryloxyproionic acids undergo intramolecular cyclization in the presence of AA.Mont.K-10 in toluene under reflux for 30–45 min in good to excellent yields. Phenyl ring bearing various substituents at the ortho, meta, para positions undergo this cyclization reaction. This method involves simple work up and amenable for large scale preparations. The heterogeneous acid treated catalyst can be regenerated and used for up to three cycles with minimum loss of activity.
Hydrated ferric sulfate-catalyzed reactions of indole with aldehydes, ketones, cyclic ketones, and chromanones: Synthesis of bisindoles and trisindoles
Noland, Wayland E.,Kumar, Honnaiah Vijay,Flick, Grant C.,Aspros, Cole L.,Yoon, Jong Hyeon,Wilt, Andre C.,Dehkordi, Nasim,Thao, Sheng,Schneerer, Andrew K.,Gao, Siming,Tritch, Kenneth J.
, p. 3913 - 3922 (2017/06/13)
Hydrated ferric sulfate [Fe2(SO4)3·xH2O] has been found to be an efficient catalyst for condensation of bisindoles or trisindoles with aliphatic or aryl aldehydes and ketones including methyl and ethyl-alkyl ketones, methyl aryl ketones, cyclic ketones, and 4-chromanones in 19–96% yields. Trisindoles and 2,2'-alkylidenebisindoles were obtained from indole-3-carbaldehydes or 3-methylindole in 72–84% yields. A total of 43 substrates was employed, giving 33 bisindoles, 3 trisindoles, and one 2:2 product; seventeen of these are new. The best results were obtained from heating ethanolic suspensions, with Fe2(SO4)3·xH2O loaded at 60 mg per mmol of electrophiles. The reaction times were typically 1–4 h, while hindered electrophiles required 8–24 h. These conditions were strong enough to promote 2:1 condensation of indole with substrates without forming higher-order byproducts, with few exceptions. This strategy features tolerance by the catalyst of a wide range of functional groups, readily available starting materials, simple operation, mild reaction conditions, and is environmentally friendly.
Synthesis, evaluation and in silico molecular modeling of pyrroyl-1,3,4-thiadiazole inhibitors of InhA
Joshi, Shrinivas D.,More, Uttam A.,Koli, Deepshikha,Kulkarni, Manoj S.,Nadagouda, Mallikarjuna N.,Aminabhavi, Tejraj M.
, p. 151 - 167 (2015/03/30)
Enoyl acyl carrier protein reductase (ENR) is an essential type II fatty acid synthase (FAS-II) pathway enzyme that is an attractive target for designing novel antitubercular agents. Herein, we report sixty-eight novel pyrrolyl substituted aryloxy-1,3,4-thiadiazoles synthesized by three-step optimization processes. Three-dimensional quantitative structure-activity relationships (3D-QSAR) were established for pyrrolyl substituted aryloxy-1,3,4-thiadiazole series of InhA inhibitors using the comparative molecular field analysis (CoMFA). Docking analysis of the crystal structure of ENR performed by using Surflex-Dock in Sybyl-X 2.0 software indicates the occupation of pyrrolyl substituted aryloxy 1,3,4-thiadiazole into hydrophobic pocket of InhA enzyme. Based on docking and database alignment rules, two computational models were established to compare their statistical results. The analysis of 3D contour plots allowed us to investigate the effect of different substituent groups at different positions of the common scaffold. In vitro testing of ligands using biological assays substantiated the efficacy of ligands that were screened through in silico methods.
