121497-03-8Relevant articles and documents
Multicomponent One-Pot Synthesis of 3-Tetrazolyl and 3-Imidazo[1,2-a]pyridin Tetrazolo[1,5-a]quinolines
Unnamatla, M. V. Basavanag,Islas-Jácome, Alejandro,Quezada-Soto, Andrea,Ramírez-López, Sandra C.,Flores-álamo, Marcos,Gámez-Monta?o, Rocío
, p. 10576 - 10583 (2016)
A series of 18 3-tetrazolyl-tetrazolo[1,5-a]quinolines were synthesized in 21-90% yields via a novel one-pot Ugi-azide/SNAr/ring-chain azido-tautomerization process. We report also the synthesis of 10 3-imidazo[1,2-a]pyridin-tetrazolo[1,5-a]quinolines in 28-94% yields via a novel one-pot Groebke-Blackburn-Bienaymé/SNAr/ring-chain azido-tautomerization process. Both synthetic strategies involve the use of microwaves or ultrasound, and catalyst-free conditions. Finally, we show the synthesis of the tetrazolo[1,5-a]quinoline-3-carbaldehyde and tetrazolo[1,5-a]quinoline-3-dimethyl acetal at room temperature in methanol as solvent.
Microwave-assisted synthesis of some new tetrazolo [1,5-α]quinoline- based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity
Mungra, Divyesh C.,Patel, Manish P.,Patel, Ranjan G.
, p. 782 - 789 (2011)
Keeping the objective to build up a new structural class of potent antimicrobials, a series of some new 4-Benzimidazol-2-yl tetrazolo[1,5-α] quinoline derivatives has been synthesized by reaction of tetrazolo[1,5- α]quinoline-4-carbaldehyde and o-phenylenediamine in the presence of an organocatalyst p-TsOH under the influence of microwave irradiation. The identity of all the compounds has been established by 1H NMR, 13C NMR, FTIR, and elemental analysis. The synthesized compounds were subjected to in vitro antimicrobial screening against a representative panel of pathogenic strains including three Gram-positive bacteria (Bacillus subtilis, Clostridium tetani, and Streptococcus pneumoniae) and three Gramnegative bacteria (Escherichia coli, Salmonella typhi, and Vibrio cholerae) as well as two fungal organisms (Aspergillus fumigatus and Candida albicans) by employing broth microdilution method. Of the compounds studied, compound 5e demonstrated significant activity against a Grampositive bacteria Bacillus subtilis. Springer Science+Business Media, LLC 2010.
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.
, p. 436 - 441 (2009)
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.
Tetrazolo[1,5-a]quinoline as a potential promising new scaffold for the synthesis of novel anti-inflammatory and antibacterial agents
Bekhit, Adnan A.,El-Sayed, Ola A.,Aboulmagd, Elsayed,Park, Ji Young
, p. 249 - 255 (2004)
Three series of tetrazolo[1,5-a]quinoline derivatives have been synthesized. The first series was synthesized starting by the condensation of tetrazolo[1,5-a]quinoline-4-carboxaldehyde 2 with substituted thiosemicarbazides, followed by cyclization of the
Synthesis and Anticancer Activity of a Novel Series of Tetrazolo[1,5-a]quinoline Based 1,2,3-Triazole Derivatives
Ganai, A. M.,Gopichand, K.,Kishan, E.,Nagaraju, R.,Rao, N. N.,Rao, P. Venkateswar
, p. 314 - 318 (2020)
Abstract: We report here the synthesis of a novel series of tetrazolo[1,5-a]quinoline based 1,2,3-triazoles from acetaniline via the Vilsmeier–Haack reaction, the Claisen–Schmidt condensation and 1,3-dipolar Click reaction. The newly synthesized compounds
Synthesis and antibacterial screening of new 4-((5-(difluoromethoxy)-1H- benzo[d]imidazol-2-ylthio)methyl)-tetrazolo[1,5-a]quinoline Derivatives
Sonar, Swapnil S.,Sadaphal, Sandip A.,Pokalwar, Rajkumar U.,Shingate, Bapurao B.,Shingare, Murlidhar S.
, p. 441 - 445 (2010)
(Chemical Equation Presented) A method for the synthesis of previously unknown heterocyclic systems 4-((5-(difluoromethoxy)-1H-benzo[ d]imidazol-2-ylthio)methyl)tetrazolo[1,5-a]quinolines derivatives 6 has been developed based on various substitutes 2-chloroquinoline-3-carbaldehydes 1 via the consecutive steps of conversion into tetrazolo[ 1,5-a]quinoline-4- carbaldehyde 2 on treatment with sodium azide which upon reduction to the corresponding alcohol derivatives 3, conversion to chlorides 4 with thionyl chloride followed by the coupling with 5-(difluoromethoxy)-1H-benzo[d]imidazole- 2-thiol 5. The synthesized titled compounds (6a-e) were screened for the antibacterial activity against gram positive and gram negative bacteria.
Dicationic liquid mediated synthesis of tetrazoloquinolinyl methoxy phenyl 4-thiazolidinones and their antibacterial and antitubercular evaluation
Deshmukh, Amarsinh R.,Dhumal, Sambhaji T.,Nawale, Laxman U.,Khedkar, Vijay M.,Sarkar, Dhiman,Mane, Ramrao A.
, p. 587 - 601 (2019)
In a search of new potentially active antitubercular agents here we have synthesized 3-substituted phenyl-2-(4-(tetrazolo[1,5-a]quinolin-4-ylmethoxy)phenyl)thiazolidin-4-ones (8a–l) and evaluated their antibacterial, particularly antitubercular activity. These have been conveniently synthesized by performing one–pot cyclocondensation of 4-(tetrazolo[1,5-a]quinolin-4-ylmethoxy)benzaldehyde, anilines and mercaptoacetic acid in dicationic ionic liquid, (3-methyl-1-[3-(methyl-1H-imidazolium-1-yl)propyl]-1H-imidazolium dibromide [C3(MIM)2–2Br]) and obtained excellent yields of (8a–l). 4-Thiazolidinones (8a–l) were thoroughly characterized by their spectral analyses. These compounds have been screened for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Ra and Mycobacterium bovis (BCG). The compounds 8a, 8c, and 8e exhibited notable in vitro antitubercular activity compare to the reference, Rifampicin. Molecular docking study has also been performed to know the binding mode of these analogs in to the active site of DprE1 enzyme. The synthesized compounds were also evaluated for their in vitro antibacterial activity and amongst them compound 8k has shown moderate activity against both gram-negative and gram-positive bacterial strains.
A novel three-component reaction: Synthesis of some complex annelated quinolines from simple acetanilides and via intramolecular 1,3-dipolar cycloaddition of azide to nitrile
Baruah, Biswajita,Deb, Mohit L.,Bhuyan, Pulak J.
, p. 1873 - 1876 (2007)
Synthesis of a novel class of tetrazolo[4′,5′:1,6]pyrido[2,3-d] quinolines from simple acetanilides and via intramolecular 1,3-dipolar cycloaddition of azides to nitriles using a three-component one-pot protocol is reported. Georg Thieme Verlag Stuttgart.
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.
, p. 243 - 249 (2010)
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.
New tetrazoloquinolinyl methoxyphenyl-4-thiazolidinones: synthesis and antihyperglycemic evaluation
Deshmukh, Amarsinh R.,Bhosle, Manisha R.,Khillare, Lalit D.,Dhumal, Sambhaji T.,Mishra, Akansha,Srivastava, Arvind K.,Mane, Ramrao A.
, p. 1107 - 1120 (2017)
Abstract: We report synthesis and in?vivo antihyperglycemic evaluation of new 3-substituted phenyl-2-(4-(tetrazolo[1,5-a]quinolin-4-ylmethoxy)phenyl)thiazolidin-4-ones (8a–l). The title 4-thiazolidinones were synthesized by one-pot cyclocondensation of new 4-(tetrazolo[1,5-a]quinolin-4-ylmethoxy)benzaldehyde (5), anilines, and mercaptoacetic acid in PEG-400. The required aldehyde (5) was also synthesized, starting from 2-chloroquinoline-3-carbaldehyde via a successive multistep route. The newly synthesized products were thoroughly characterized based on their spectral data. Amongst them, compounds 8a–g, j exhibited notable in?vivo antihyperglycemic activity. Compounds 8f, g showed percentage improvement in oral glucose tolerance of 18.9 and 20.7, respectively, compared with 28.3 for the reference metformin. Graphical Abstract: [Figure not available: see fulltext.]
