Ethyl gallate isolated from phenol-enriched fraction of Caesalpinia mimosoides Lam. Promotes cutaneous wound healing: a scientific validation through bioassay-guided fractionation Pradeep Bhat, Vishal S. Patil, Ashish Anand, Subhas Bijjaragi, Ganesh R. Hegde, Harsha V. Hegde, Subarna Roy Frontiers in Pharmacology, 2023 The tender shoots of Caesalpinia mimosoides Lam. are used ethnomedically by the traditional healers of Uttara Kannada district, Karnataka (India) for the treatment of wounds. The current study was aimed at exploring phenol-enriched fraction (PEF) of crude ethanol extract of tender shoots to isolate and characterize the most active bio-constituent through bioassay-guided fractionation procedure. The successive fractionation and sub-fractionation of PEF, followed by in vitro scratch wound, antimicrobial, and antioxidant activities, yielded a highly active natural antioxidant compound ethyl gallate (EG). In vitro wound healing potentiality of EG was evidenced by a significantly higher percentage of cell migration in L929 fibroblast cells (97.98 ± 0.46% at 3.81 μg/ml concentration) compared to a positive control group (98.44 ± 0.36%) at the 48th hour of incubation. A significantly higher rate of wound contraction (98.72 ± 0.41%), an elevated tensile strength of the incised wound (1,154.60 ± 1.42 g/mm2), and increased quantity of connective tissue elements were observed in the granulation tissues of the 1% EG ointment treated animal group on the 15th post-wounding day. The accelerated wound healing activity of 1% EG was also exhibited by histopathological examinations through Hematoxylin and Eosin, Masson’s trichome, and Toluidine blue-stained sections. Significant up-regulation of enzymatic and non-enzymatic antioxidant contents (reduced glutathione, superoxide dismutase, and catalase) and down-regulation of oxidative stress marker (lipid peroxidation) clearly indicates the effective granular antioxidant activity of 1% EG in preventing oxidative damage to the skin tissues. Further, in vitro antimicrobial and antioxidant activities of EG supports the positive correlation with its enhanced wound-healing activity. Moreover, molecular docking and dynamics for 100 ns revealed the stable binding of EG with cyclooxygenase-2 (−6.2 kcal/mol) and matrix metalloproteinase-9 (−4.6 kcal/mol) and unstable binding with tumor necrosis factor-α (−7.2 kcal/mol), suggesting the potential applicability of EG in inflammation and wound treatment.
Enhanced proton conductivity in amino acid based self-assembled non-porous hydrogen-bonded organic frameworks Titas Pramanik, Ashish Anand, Ajmal Pandikassala, Rajith Illathvalappil, Sreekumar Kurungot, T. N. Guru Row Chemical Communications, 2022 Amino acid and oxalic acid-based salt-cocrystals have been discovered as non-porous self-assembled HOFs that show efficient proton conductivity under humidified conditions. Promising performance as a membrane in H2–O2 fuel cells has been achieved.
Comparative Investigation on the Crystal Structures, Hirshfeld Surface Analysis, Antitubercular Assays, and Molecular Docking of Regioisomeric 1,2,3-Triazoles Ashish Anand, Kishorkumar Sindogi, Sheshagiri R. Dixit, Richa P. Shetty, Gurubasavaraj V. Pujar, Manohar V. Kulkarni, Tayur N. Guru Row Chemistryselect, 2022 Abstract 1,2,3‐triazole system is readily obtained by the click reaction in a facile and regioselective way. Regioselectivity is introduced under Copper(CuAAC), and Ruthenium(RuAAC) catalysed azide‐alkyne cycloaddition reaction furnishing 1,4 and 1,5‐disubstituted triazoles, respectively. These two regioisomeric systems offer discrete physicochemical and medicinal properties based on crucial binding interactions and biocompatibility with the biological targets. In this regard, a comparative investigation on the coumarin‐linked regioisomeric 1,2,3‐triazoles via its crystal structure, Hirshfeld surface analysis, and antitubercular assays and molecular docking are reported. It sheds light on the variation of in vitro antitubercular efficacy against Mycobacterium tuberculosis H 37 Rv followed by molecular docking studies that justify the prominent interactions at the binding site. Further, solid‐state and Hirshfeld surface analysis provided significant crystallographic insights on the critical intermolecular interactions that dictate the crystal packing in these systems. Thus structure‐property correlation for these regioisomeric systems can open new avenues in drug design and discovery.
Biheterocyclic Coumarins: A Simple yet Versatile Resource for Futuristic Design and Applications in Bio-molecular and Material Chemistry Ashish Anand, Netravati Khanapurmath, Manohar V. Kulkarni, Tayur N. Guru Row Current Organic Chemistry, 2022 Coumarin derivatives occur widely in nature and are a part of both traditional and modern advancements in synthesis and application. To date, thousands of coumarin derivatives have been synthesized in lab or isolated from plant and marine life. These are essentially 2- pyrone core fused with a benzene ring and belong to the family of aromatic oxygen heterocycles. Coumarin in conjugation with various other heterocyclic systems has provided a robust framework for tuning the properties associated with the parent structure. The frequency of reports has increased for these biheterocyclic systems from the mid twentieth century. Biheterocyclic coumarins have also attracted the attention of many organic and pharmaceutical chemists as these systems serve as useful synthetic intermediates in the synthesis of analogs of existing drugs. Their application in the design of effective organocatalysts and chemosensors has further extended their versatility. Coumarin biheterocyclic core is utilized in the rational design and tuning of complex molecular entities in molecular recognition, analytical and material chemistry. This review highlights the advancements in the synthesis and applications of coumarin-linked nitrogen, oxygen, and sulfur heterocycles. It also provides an account of five-, six-, and seven-membered heterocyclic rings linked to coumarin core. Critical physicochemical properties coupled with their application will make this review useful for synthetic chemists and drug discovery labs. A comprehensive spectrum of literature in this review will facilitate further development of biheterocycles along with their promising applications in the future.
WELPSA: A natural catalyst of alkali and alkaline earth metals for the facile synthesis of tetrahydrobenzo[b]pyrans and pyrano[2,3-d]pyrimidinones as inhibitors of SARS-CoV-2 Aravind R. Nesaragi, Ravindra R. Kamble, Swati R. Hoolageri, Ahmedraza Mavazzan, Suresh F. Madar, Ashish Anand, Shrinivas D. Joshi Applied Organometallic Chemistry, 2022 Since 2019, the infection of SARS‐CoV‐2 has been spreading worldwide and caused potentially lethal health problems. In view of this, the present study explores the most commodious and environmentally benign synthetic protocol for the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3‐d]pyrimidinones as SARS‐CoV‐2 inhibitors via three‐component cycloaddition of aromatic aldehyde, malononitrile, and dimedone/barbituric acid in water. Lemon peel from juice factory waste, namely, lemon ( Citrus limon ), sweet lemon ( C. limetta ), and Kaffir lime or Citron ( C. hystrix ), effectually utilized to obtain WELPSA, WESLPSA, and WEKLPSA, respectively, for the synthesis of title compounds. The catalyst was characterized by scanning electron microscope (SEM) and energy‐dispersive x‐ray spectroscopy (EDX). The concentration of sodium, potassium, calcium, and magnesium in the catalyst (WELPSA) was determined using atomic absorption spectrometry (AAS). The current approach manifests numerous notable advantages that include ease of preparation, handling and benignity of the catalyst, low cost, green reaction conditions, facile workup, excellent yields (93%–97%) with extreme purity, and recyclability of the catalyst. Compounds were docked on the crystal structure of SARS‐CoV‐2 (PDB: 6M3M). The consensus score obtained in the range 2.47–4.63 suggests that docking study was optimistic indicating the summary of all forces of interaction between ligands and the protein.
Click chemistry approach for the regioselective synthesis of iso-indoline-1,3-dione-linked 1,4 and 1,5 coumarinyl 1,2,3-triazoles and their photophysical properties Ashish Anand, Manohar V. Kulkarni Synthetic Communications, 2017 Copper-catalyzed reaction of N-propargyl isoindoline-1,3-dione and 4-azidomethyl coumarins / 4-azidomethyl-1-aza coumarins under click chemistry conditions afforded 1,4-disubstituted 1,2,3-triazoles, whereas ruthenium catalysis yielded isomeric 1,5-disubstituted 1,2,3-triazoles. The two regioisomers have been distinguished by NOE studies. UV absorption for a given pair of isomers exhibited similar trend, whereas fluorescence measurements showed considerable differences. Photo physical studies on the interaction of azides with copper and ruthenium have also been performed. GRAPHICAL ABSTRACT
Synthesis and anti-bacterial evaluation of 4-aryloxymethyl carbostyrils derived from substructures and degradation products of Vancomycin Indian Journal of Chemistry Section B Organic and Medicinal Chemistry, 2016
One pot Click chemistry: A three component reaction for the synthesis of 2-mercaptobenzimidazole linked coumarinyl triazoles as anti-tubercular agents Ashish Anand, Manohar V. Kulkarni, Shrinivas D. Joshi, Sheshagiri R. Dixit Bioorganic and Medicinal Chemistry Letters, 2016 2-Propargylthiobenzimidazole 1, 4-bromomethyl coumarins/1-aza-coumarins 2/3 and sodium azide have been reacted in one pot under Click chemistry conditions to give exclusively 1,4-disubstituted triazoles 5a-n. Anti-tubercular assays against M. tuberculosis (H37Rv) coupled with in silico molecular docking studies indicated that dimethyl substituents 5c and 5d showed promising activity with higher C-score values.
A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents Ashish Anand, Reshma J. Naik, Hrishikesh M. Revankar, Manohar V. Kulkarni, Sheshagiri R. Dixit, Shrinivas D. Joshi European Journal of Medicinal Chemistry, 2015 A series of mono and bis-triazole coumarin hybrids 6a-u and 9a-f respectively have been synthesized using 4-(azidomethyl)-2H-chromen-2-ones 5a-i and aryl propargyl ethers 2a-c/8 employing Click chemistry modified protocol for Azide-Alkyne cycloadditions(CuAAC). Anti-tubercular screening showed moderate activity for mono aryloxy compounds 6a-u with MIC 50-100 μg/mL, whereas the bis compounds 9a-f were more effective with MICs between 0.2 and 12.5 μg/mL. Molecular modeling and 3D-QSAR measurements using CoMFA and Topomer CoMFA further supported the observed results. The bis compound 9b showed excellent activity with MIC value as low as 0.2 μg/mL.
RECENT SCHOLAR PUBLICATIONS
Selective capture, isolation, and characterization of mucin foraging neu-raminidase-active bacteria from microbiomes using a non-inhibitory activ-ity-based probe K Shipman, A Steiger, E Ugwuoji, L Webber, A Anand, A Wright ChemRxiv 2024 (1115) , 2024 2024
Ethyl gallate isolated from phenol-enriched fraction of Caesalpinia mimosoides Lam. Promotes cutaneous wound healing: a scientific validation through bioassay … P Bhat, VS Patil, A Anand, S Bijjaragi, GR Hegde, HV Hegde, S Roy Frontiers in pharmacology 14, 1214220 , 2023 2023 Citations: 15
Single-crystal XRD, Hirshfeld surfaces, 3D energy framework calculations, and DFT studies of 4, 5-diphenyl-1, 3, 4-thiadiazole-2-thiolate: A mesoionic compound T Vishwanath, A Ashish, CKR Shankar, KD Amar Journal of Molecular Structure 1264, 133290 , 2022 2022 Citations: 20
Comparative investigation on the crystal structures, Hirshfeld surface analysis, antitubercular assays, and molecular docking of regioisomeric 1, 2, 3‐triazoles A Anand, K Sindogi, SR Dixit, RP Shetty, GV Pujar, MV Kulkarni, ... ChemistrySelect 7 (15), e202104352 , 2022 2022 Citations: 3
Chitosan‐ZnO: An Efficient and Recyclable Polymer Incorporated Hybrid Nanocatalyst to Synthesize Tetrahydrobenzo[ b ]pyrans and Pyrano[2,3‐ d ]pyrimidinones … AR Nesaragi, T Gasti, TV Metre, A Anand, RR Kamble, RB Chougale, ... ChemistrySelect 7 (14), e202200604 , 2022 2022 Citations: 17
Biheterocyclic coumarins: A simple yet versatile resource for futuristic design and applications in bio-molecular and material chemistry A Anand, N Khanapurmath, MV Kulkarni, TN Guru Row Current Organic Chemistry 26 (5), 444-506 , 2022 2022 Citations: 18
Enhanced proton conductivity in amino acid based self-assembled non-porous hydrogen-bonded organic frameworks T Pramanik, A Anand, A Pandikassala, R Illathvalappil, S Kurungot, ... Chemical Communications 58 (40), 5972-5975 , 2022 2022 Citations: 7
WELPSA: A natural catalyst of alkali and alkaline earth metals for the facile synthesis of tetrahydrobenzo[ b ]pyrans and pyrano[2,3‐ d ]pyrimidinones as inhibitors of … AR Nesaragi, RR Kamble, SR Hoolageri, A Mavazzan, SF Madar, ... Applied Organometallic Chemistry 36 (1), e6469 , 2022 2022 Citations: 38
Organic eutectics: characterization, micro-structural evolution and properties. T Pramanik, A Anand, J Sunil, A Joseph, C Narayana, S Dutta, TNG Row Acta Cryst 77, C121 , 2021 2021
Fluorescence Investigations on Interactions between 7,8-benzo-4-azidomethyl Coumarin and Ortho - and Para -phenylenediamines in Binary Solvent Mixtures of … JM Nirupama, LS Chougala, NI Khanapurmath, A Ashish, LA Shastri, ... Journal of Fluorescence 28 (1), 359-372 , 2018 2018 Citations: 6
Click chemistry approach for the regioselective synthesis of iso-indoline-1, 3-dione-linked 1, 4 and 1, 5 coumarinyl 1, 2, 3-triazoles and their photophysical properties A Anand, MV Kulkarni Synthetic Communications 47 (7), 722-733 , 2017 2017 Citations: 22
One pot Click chemistry: A three component reaction for the synthesis of 2-mercaptobenzimidazole linked coumarinyl triazoles as anti-tubercular agents A Anand, MV Kulkarni, SD Joshi, SR Dixit Bioorganic & Medicinal Chemistry Letters 26 (19), 4709-4713 , 2016 2016 Citations: 68
Synthesis and anti-bacterial evaluation of 4-aryloxymethyl carbostyrils derived from substructures and degradation products of Vancomycin HM Revankar, S Arali, S Yakkerimath, PP Revankar, V Naik, A Anand, ... Indian Journal of Chemistry 55, 637-642 , 2016 2016
Cyclopropanes in water: a diastereoselective synthesis of substituted 2 H-chromen-2-one and quinolin-2 (1 H)-one linked cyclopropanes A Anand, J Yenagi, J Tonannavar, MV Kulkarni Green Chemistry 18 (7), 2201-2205 , 2016 2016 Citations: 12
A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents A Anand, RJ Naik, HM Revankar, MV Kulkarni, SR Dixit, SD Joshi European journal of medicinal chemistry 105, 194-207 , 2015 2015 Citations: 84
MOST CITED SCHOLAR PUBLICATIONS
A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents A Anand, RJ Naik, HM Revankar, MV Kulkarni, SR Dixit, SD Joshi European journal of medicinal chemistry 105, 194-207 , 2015 2015 Citations: 84
One pot Click chemistry: A three component reaction for the synthesis of 2-mercaptobenzimidazole linked coumarinyl triazoles as anti-tubercular agents A Anand, MV Kulkarni, SD Joshi, SR Dixit Bioorganic & Medicinal Chemistry Letters 26 (19), 4709-4713 , 2016 2016 Citations: 68
WELPSA: A natural catalyst of alkali and alkaline earth metals for the facile synthesis of tetrahydrobenzo[ b ]pyrans and pyrano[2,3‐ d ]pyrimidinones as inhibitors of … AR Nesaragi, RR Kamble, SR Hoolageri, A Mavazzan, SF Madar, ... Applied Organometallic Chemistry 36 (1), e6469 , 2022 2022 Citations: 38
Click chemistry approach for the regioselective synthesis of iso-indoline-1, 3-dione-linked 1, 4 and 1, 5 coumarinyl 1, 2, 3-triazoles and their photophysical properties A Anand, MV Kulkarni Synthetic Communications 47 (7), 722-733 , 2017 2017 Citations: 22
Single-crystal XRD, Hirshfeld surfaces, 3D energy framework calculations, and DFT studies of 4, 5-diphenyl-1, 3, 4-thiadiazole-2-thiolate: A mesoionic compound T Vishwanath, A Ashish, CKR Shankar, KD Amar Journal of Molecular Structure 1264, 133290 , 2022 2022 Citations: 20
Biheterocyclic coumarins: A simple yet versatile resource for futuristic design and applications in bio-molecular and material chemistry A Anand, N Khanapurmath, MV Kulkarni, TN Guru Row Current Organic Chemistry 26 (5), 444-506 , 2022 2022 Citations: 18
Chitosan‐ZnO: An Efficient and Recyclable Polymer Incorporated Hybrid Nanocatalyst to Synthesize Tetrahydrobenzo[ b ]pyrans and Pyrano[2,3‐ d ]pyrimidinones … AR Nesaragi, T Gasti, TV Metre, A Anand, RR Kamble, RB Chougale, ... ChemistrySelect 7 (14), e202200604 , 2022 2022 Citations: 17
Ethyl gallate isolated from phenol-enriched fraction of Caesalpinia mimosoides Lam. Promotes cutaneous wound healing: a scientific validation through bioassay … P Bhat, VS Patil, A Anand, S Bijjaragi, GR Hegde, HV Hegde, S Roy Frontiers in pharmacology 14, 1214220 , 2023 2023 Citations: 15
Cyclopropanes in water: a diastereoselective synthesis of substituted 2 H-chromen-2-one and quinolin-2 (1 H)-one linked cyclopropanes A Anand, J Yenagi, J Tonannavar, MV Kulkarni Green Chemistry 18 (7), 2201-2205 , 2016 2016 Citations: 12
Enhanced proton conductivity in amino acid based self-assembled non-porous hydrogen-bonded organic frameworks T Pramanik, A Anand, A Pandikassala, R Illathvalappil, S Kurungot, ... Chemical Communications 58 (40), 5972-5975 , 2022 2022 Citations: 7
Fluorescence Investigations on Interactions between 7,8-benzo-4-azidomethyl Coumarin and Ortho - and Para -phenylenediamines in Binary Solvent Mixtures of … JM Nirupama, LS Chougala, NI Khanapurmath, A Ashish, LA Shastri, ... Journal of Fluorescence 28 (1), 359-372 , 2018 2018 Citations: 6
Comparative investigation on the crystal structures, Hirshfeld surface analysis, antitubercular assays, and molecular docking of regioisomeric 1, 2, 3‐triazoles A Anand, K Sindogi, SR Dixit, RP Shetty, GV Pujar, MV Kulkarni, ... ChemistrySelect 7 (15), e202104352 , 2022 2022 Citations: 3
Selective capture, isolation, and characterization of mucin foraging neu-raminidase-active bacteria from microbiomes using a non-inhibitory activ-ity-based probe K Shipman, A Steiger, E Ugwuoji, L Webber, A Anand, A Wright ChemRxiv 2024 (1115) , 2024 2024
Organic eutectics: characterization, micro-structural evolution and properties. T Pramanik, A Anand, J Sunil, A Joseph, C Narayana, S Dutta, TNG Row Acta Cryst 77, C121 , 2021 2021
Synthesis and anti-bacterial evaluation of 4-aryloxymethyl carbostyrils derived from substructures and degradation products of Vancomycin HM Revankar, S Arali, S Yakkerimath, PP Revankar, V Naik, A Anand, ... Indian Journal of Chemistry 55, 637-642 , 2016 2016