80231-50-1Relevant academic research and scientific papers
Novel tetrazoloquinoline-rhodanine conjugates: Highly efficient synthesis and biological evaluation
Subhedar, Dnyaneshwar D.,Shaikh, Mubarak H.,Nawale, Laxman,Yeware, Amar,Sarkar, Dhiman,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Shingate, Bapurao B.
supporting information, p. 2278 - 2283 (2016/04/20)
In search of new active molecules against Mycobacterium tuberculosis (MTB) H37Ra and Mycobacterium bovis BCG, a small focused library of rhodanine incorporated tetrazoloquinoline has been efficiently synthesized by using [HDBU][HSO4] acidic ionic liquid. The compound 3c found to be promising inhibitor of MTB H37Ra and M. bovis BCG characterized by lower MIC values 4.5 and 2.0 μg/mL, respectively. The active compounds were further tested for cytotoxicity against HeLa, THP-1, A549 and PANC-1 cell lines using MTT assay and showed no significant cytotoxic activity at the maximum concentration evaluated. Again, the synthesized compounds were found to have potential antifungal activity. Furthermore, to rationalize the observed biological activity data, the molecular docking study also been carried out against a potential target Zmp1 enzyme of MTB H37Ra, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of in vitro and in silico study suggest that these compounds possess ideal structural requirement for the further development of novel therapeutic agents.
Novel tetrazoloquinoline-thiazolidinone conjugates as possible antitubercular agents: Synthesis and molecular docking
Subhedar, Dnyaneshwar D.,Shaikh, Mubarak H.,Shingate, Bapurao B.,Nawale, Laxman,Sarkar, Dhiman,Khedkar, Vijay M.
supporting information, p. 1832 - 1848 (2016/09/28)
A novel approach for the synthesis of a new 4-thiazolidinone scaffold was developed by a one-pot three-component cyclocondensation of various tetrazolo quinoline aldehydes 1a-f, acid hydrazide 2a-c, and thioglycolic acid 3 in the presence of [DBUH][OAc] as a catalyst in high yields. All the conjugates were screened for their antimycobacterial activity against MTB H37Ra and M. bovis BCG strains, with the MIC values ranging from 0.99-13.55 μmol mL-1 and 0.14-20.11 μmol mL-1, respectively. The 4-thiazolidinone-incorporated tetrazoloquinoline derivatives 4a, 4d, 4g, 4j, 4m, and 4p were highly potent against MTB H37Ra and M. bovis BCG strains. The most active compounds were also evaluated for their cytotoxicity against MCF-7, A549, and HCT 116 cell lines and were found to be non-cytotoxic. Further, molecular docking studies into the active site of the InhA enzyme revealed a similar binding mode to the native ligand in the crystal structure, thereby helping us to understand the ligand-protein binding interaction and establish a structural basis for the inhibition of mycobacterium tuberculosis. The results suggest that the tetrazoloquinoline-thiazolidinone conjugates 4a, 4d, 4g, 4j, 4m, and 4p are promising antitubercular agents.
Novel amalgamation of phthalazine–quinolines as biofilm inhibitors: One-pot synthesis, biological evaluation and in silico ADME prediction with favorable metabolic fate
Zaheer, Zahid,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Patil, Rajendra H.,Lohar
, p. 1696 - 1703 (2016/07/27)
A facile and highly efficient one-pot synthesis of phthalazine–quinoline derivatives is reported via four component reaction of phthalic anhydride, hydrazine hydrate, 5,5-dimethyl 1,3 cyclohexanedione and various quinoline aldehydes using PrxCoFe2?xO4(x?=?0.1) nanoparticles as a catalyst. The synthesized compounds have been evaluated for anti-biofilm activity against Pseudomonas aeruginosa and Candida albicans. The compounds 12a (IC50?=?30.0?μM) and 12f (IC50?=?34.5?μM) had shown promising anti-biofilm activity against P. aeruginosa and C. albicans, respectively, when compared with standards without affecting the growth of cells (and thus behave as anti-quorum sensing agents). Compounds 12a (MIC?=?45.0?μg/mL) and 12f (MIC?=?57.5?μg/mL) showed significant potent antimicrobial activity against P. aeruginosa and C. albicans, respectively. Thus, the active derivatives were not only potent biofilm inhibitors but also efficient antimicrobial agents. In silico ADME and metabolic site prediction studies were also held out to set an effective lead candidate for the future antimicrobial drug discovery initiatives.
Synthesis, in vitro antibacterial and antifungal evaluations of new α-hydroxyphosphonate and new α-acetoxyphosphonate derivatives of tetrazolo [1, 5-a] quinoline
Kategaonkar, Amol H.,Pokalwar, Rajkumar U.,Sonar, Swapnil S.,Gawali, Vaibhav U.,Shingate, Bapurao B.,Shingare, Murlidhar S.
scheme or table, p. 1128 - 1132 (2010/04/24)
A series of new α-hydroxyphosphonate and α-acetoxyphosphonate derivatives have been synthesized for the first time of tetrazolo [1, 5-a] quinoline derivatives. Elemental analysis, IR, 1H NMR, 13C NMR and mass spectral data elucidated the structures of the all newly synthesized compounds. In vitro antimicrobial activities of the synthesized compounds were investigated against Gram-positive Bacillus subtilis, Gram-negative Escherichia coli and fungi Candida albicans and Aspergillus niger. Some of the tested compounds showed significant antimicrobial activity.
Synthesis and in vitro antimicrobial activity of new ethyl 2-(Ethoxyphosphono)-1-cyano-2-(substituted tetrazolo-[1,5-a]quinolin-4-yl)ethanoate derivatives
Kategaonkar, Amol H.,Sadaphal, Sandip A.,Shelke, Kiran F.,Kategaonkar, Atul H.,Shingate, Bapurao B.,Shingare, Murlidhar S.
scheme or table, p. 243 - 249 (2010/11/03)
A series of new ethyl 2-(ethoxyphosphono)-1-cyano-2-(substituted tetrazolo[1,5-a]quinolin-4-yl)ethanoate derivatives have been synthesized for the first time of tetrazolo[1,5-a]quinoline derivatives. Elemental analysis, IR, 1H NMR, 13C NMR, 31P NMR and mass spectral data elucidated the structures of the all newly synthesized compounds. In vitro antimicrobial activities of synthesized compounds have been investigated against Gram-positive Bacillus subtilis, Gram-negative Escherichia coli and two fungi Candida albicans and Aspergillus niger in comparison with standard drugs. Significantly microbiological behavior of these newly synthesized derivatives possesses significant antibacterial and antifungal activity.
Synthesis and in vitro antimicrobial activity of new α- aminophosphonates via tetrazolo [1,5-a] quinoline derivatives
Kategaonkar, Amol H.,Sonar, Swapnil S.,Sapkal, Suryakant B.,Gawali, Vaibhav U.,Shingate, Bapurao B.,Shingare, Murlidhar S.
scheme or table, p. 2113 - 2121 (2010/12/18)
A series of diethyl (4-fluorophenylamino) (substituted tetrazolo[1,5-a] quinolin-4-yl)methyl phosphonate derivatives has been synthesized for the first time from tetrazolo [1,5-a] quinoline derivatives. Elemental analysis, IR, 1H NMR, 13C NMR, and mass spectral data elucidated the structures of the all newly synthesized compounds. In vitro antimicrobial activities of synthesized compounds have been investigated against Gram-positive Bacillus subtilis, Gram-negative Escherichia coli, and two fungi Candida albicans and Aspergillus niger in comparison with standard drugs. Significantly, microbiological behavior of these newly synthesized derivatives possesses significant antibacterial and antifungal activity. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
Synthesis and antimicrobial activity of tetrazolo[1,5-a]-quinoline-4- carbonitrile derivatives
Kategaonkar, Amol H.,Labade, Vilas B.,Shinde, Pravin V.,Kategaonkar, Atul H.,Shingate, Bapurao B.,Shingare, Murlidhar S.
scheme or table, p. 787 - 791 (2011/06/27)
A series of new tetrazolo[1,5-a]quinoline-4-carbonitrile derivatives were synthesized for the first time via tetrazolo[1,5-a]quinoline derivatives. Elemental analysis, IR, 1H NMR, 13C NMR, and mass spectral data were used to elucidate the structures of all newly synthesized compounds. In vitro antimicrobial activities of synthesized compounds were investigated against Gram-positive Bacillus subtilis, Gram-negative Escherichia coli, and two fungi, Candida albicans and Aspergillus niger, in comparison with standard drugs. Some of the tested compounds showed significant antimicrobial activity. Springer-Verlag 2010.
Synthesis of Schiff s bases of 8-methyl-tetrazolo[1,5-a]quinoline as potential antiinflammatory and antimicrobial agents
Bawa, Sandhya,Kumar, Suresh
experimental part, p. 142 - 145 (2009/12/04)
A series of 4-substituted-imino-methyltetrazolo[1,5-a]quinoline derivatives reported have been synthesized by condensation of 4-formyl-8-methyltetrazolo[1, 5-a]quinoline with appropriate aromatic amine by refluxing in dioxane. All the compounds have been characterized by IR, 1H NMR and mass spectroscopy and have been evaluated for their anti-inflammatory and antimicrobial activities.
Synthesis and characterization of new O, O-Diethyl phosphorothioates derived from substituted tetrazolo [1, 5-a] Quinolin- 4-Ylmethanol derivatives
Kategaonkar, Amol H.,Pokalwar, Rajkumar U.,Sadaphal, Sandip A.,Shinde, Pravin V.,Shingate, Bapurao B.,Shingare, Murlidhar S.
scheme or table, p. 436 - 441 (2010/07/16)
A simple and convenient method is developed for the synthesis of new O, O-diethyl 0-(substituted tetrazolo[1, 5-a] quinolin-4-yl) methyl phosphorothioates, which has been synthesized for the first time from tetrazolo [1,5-a] quinolines via tetrazolo [1,5-a] quinolin-4-ylmethanol derivatives. The structures of the all newly synthesized compounds were elucidated by analytical and spectral methods.
