title: One-pot synthesis, biological evaluation, and docking study of new chromeno-annulated thiopyrano[2,3-c]pyrazoles.
abstract: A one-pot synthesis of new chromeno-annulated thiopyrano[2,3-c]pyrazoles has been achieved through a domino-Knoevenagel-hetero-Diels-Alder reaction after combining various pyrazol-5-thiones with O-alkenyloxy/alkynyloxy-salicylaldehydes/naphthaldehydes in a Brønsted acidic ionic liquid, [Hmim]HSO[Formula: see text], methylimidazolium hydrogen sulphate, under microwave irradiation. The method is simple and in many cases the isolated products did not require further purification. The central pyranothiopyranyl cis-fusion was confirmed by 2D NMR NOESY and single-crystal X-ray analysis suggesting that the endo-E-Syn transition state would be the most favored pathway of the reaction. Many heterocycles of this new series were found active against six bacterial and two fungal strains. In addition, all the compounds possess good anti-oxidant activity with the ferric reducing anti-oxidant power value [Formula: see text]. All new structures were docked into active site of angiotensin I converting enzyme (ACE), assuming that the compounds possessed the anti-hypertensive activity potential on the basis of prediction of activity spectra of substances prediction results. Pyranyl ring oxygen in compound 9a forms two hydrogen bonds with HIS353 and HIS513 residues in the active site of the ACE having good G score ([Formula: see text]) of this compound, comparable to that of the reference drug captopril ([Formula: see text]).
authors.affiliation: Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Anand District, Gujarat, 388 120, India.
authors.forename: Bhagyashri D
authors.initials: BD
authors.lastname: Parmar
authors.affiliation: Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Anand District, Gujarat, 388 120, India.
authors.forename: Tushar R
authors.initials: TR
authors.lastname: Sutariya
authors.affiliation: Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Anand District, Gujarat, 388 120, India.
authors.forename: Gaurangkumar C
authors.initials: GC
authors.lastname: Brahmbhatt
authors.affiliation: Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Anand District, Gujarat, 388 120, India. njpchemdeptspu@yahoo.co.in.
authors.forename: Narsidas J
authors.initials: NJ
authors.lastname: Parmar
authors.affiliation: Department of Physics, University of Jammu, Jammu Tawi, 180 006, India.
authors.forename: Rajni
authors.initials: R
authors.lastname: Kant
authors.affiliation: Department of Physics, University of Jammu, Jammu Tawi, 180 006, India.
authors.forename: Vivek K
authors.initials: VK
authors.lastname: Gupta
authors.affiliation: Faculty of Pharmacy, The Maharaja Sayajirao University of Baroda, Vadodara, 390 001, India.
authors.forename: Prashant R
authors.initials: PR
authors.lastname: Murumkar
authors.affiliation: Faculty of Pharmacy, The Maharaja Sayajirao University of Baroda, Vadodara, 390 001, India.
authors.forename: Mayank Kumar
authors.initials: MK
authors.lastname: Sharma
authors.affiliation: Faculty of Pharmacy, The Maharaja Sayajirao University of Baroda, Vadodara, 390 001, India.
authors.forename: Mange Ram
authors.initials: MR
authors.lastname: Yadav
mesh_terms: D000803:Angiotensin I / Q000378:metabolism; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020134:Catalytic Domain / Q000187:drug effects; D061565:Cycloaddition Reaction; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D000975:Antioxidants; D001578:Benzopyrans; D011720:Pyrazoles; D000803:Angiotensin I
keywords: Docking; Domino-Knoevenagel–hetero-Diels–Alder reaction; Ionic liquid; Microwave synthesis; Pyrazole-5-thione; Thiopyrano[2, 3-c]pyrazole; [Hmim]HSO