Synthesis and antimycobacterial evaluation of various 6-substituted pyrazolo[3,4-<i>d</i>]pyrimidine derivatives

Trivedi, Anjali; Vaghasiya, Shailesh; Dholariya, Bipin H.; Dodiya, Dipti K.; Shah, V. H.

doi:10.3109/14756360903540276

Cited by 16 publications

(4 citation statements)

References 15 publications

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“…Additionally, a phenothiazine clubbed pyrazolo [3,4-d]pyrimidines 98a-c was developed and the ability of them to inhibit the growth of Mycobacterium tuberculosis in vitro was determined and the results revealed that compounds 98a-c showed a brilliant antimycobacterial activity at MIC values which were less than 6.25 µg/ml. (Trivedi et al, 2010)…”

Section: (Moukha Et Al 2000)mentioning

confidence: 99%

A review on Synthesis and Biological Evaluations of Pyrazolo[3,4-d]pyrimidine Schaffold

Salem¹,

Salem²,

Sabbagh

et al. 2022

Records of Pharmaceutical and Biomedical Sciences

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Pyrazolo [3,4-d]pyrimidine is a bicyclic hetero organic nucleus that encompass a pyrazole ring fusion with a pyrimidine ring. Pyrazolo [3,4-d]pyrimidine nucleus could be synthesized using different synthetic procedures depending on either pyrazole or pyrimidine rings as starting synthones in addition to, different miscellaneous procedures. It was initially synthesized and evaluated as adenosine nucleoside analogues for cancer and viral therapy. Recently, numerous pyrazolo [3,4-d]pyrimidine compounds adopted anti-neoplastic activity via several mechanistic pathways. Also, designing drugs with pyrazolo [3,4-d]pyrimidine nucleus as pharmacophore encourage different biological activities such as anti-inflammatory, anti-microbial, antimycobacterial, anti-malarial, anti-gout and anti-diabetic. This bibliographic development presents an overview on works carried out on pyrazolo [3,4d]pyrimidine derivatives during the period 2017-2021.

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Section: (Moukha Et Al 2000)mentioning

confidence: 99%

A review on Synthesis and Biological Evaluations of Pyrazolo[3,4-d]pyrimidine Schaffold

Salem¹,

Salem²,

Sabbagh

et al. 2022

Records of Pharmaceutical and Biomedical Sciences

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“…A diversity of biological effects is associated with pyrazolo[3,4- d ]pyrimidines. They are known to exhibit antiviral [ 111 – 112 ], pesticidal [ 113 ], anti-inflammatory [ 114 ], antimicrobial [ 115 – 117 ], antileukemic [ 118 ], antitumor [ 114 , 119 – 120 ], pan-RAF inhibiting [ 121 ], tyrosine kinase RET inhibiting [ 122 ], CNS [ 123 ], cardiovascular [ 124 – 125 ] and tuberculostatic [ 126 – 127 ] activities. The promising therapeutic potential of pyrazolo[3,4-d]pyrimidines prompted researchers to develop novel synthetic strategies to provide this class of compounds.…”

Section: Reviewmentioning

confidence: 99%

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

Aggarwal

Kumar

2018

Beilstein J. Org. Chem.

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The condensation of 5-aminopyrazole with various bielectrophilic moieties results in the formation of pyrazoloazines, an interesting array of fused heterocyclic systems. The development of new synthetic routes towards pyrazoloazines for their biological and medicinal exploration is an attractive area for researchers throughout the world. The present review focuses on various synthetic methods developed in the last decade for the synthesis of differently substituted pyrazoloazines by a broad range of organic reactions by means of 5-aminopyrazole as a precursor. ReviewPyrazole and its derivatives are known to exhibit significant biological and pharmacological activities such as: anticancer [1,2], anti-inflammatory [3,4], antioxidant [5], antibacterial [6][7][8], analgesic [9], antiviral [10,11], antimicrobial [12,13], antifungal [6], antiglycemic [14], antiamoebic [15] and antidepressive [16,17]. Considering the immense biological properties pyrazole is one of the most widely studied nitrogen-containing heterocyclic nuclei. Fused pyrazole derivatives are composed of the pyrazole nucleus attached to other heterocyclic moieties which enable them to exhibit improved pharmacological activities compared to the isolated fragments. These compounds are currently used in several marketed drugs like cartazolate (1), zaleplon (2), sildenafil (3), allopurinol (4), indiplon (5), etazolate (6) etc. (Figure 1). Fused pyrazole derivatives, especially pyrazoloazines have been reported to mimic purine bases, present in DNA and RNA, due to close structural resemblance.In addition to the immense biological potential related to fused pyrazoles, their synthetic potential needs to be reviewed for further improvements and extension of interests. Various efforts have been developed for the synthesis of pyrazole-based fused heterocycles. 5-Aminopyrazoles have been extensively employed as useful synthons in designing and constructing a Beilstein J. Org. Chem. 2018, 14, 203-242. 204 A number of review articles have been published by us and others highlighting the synthetic and biological aspects of 5-aminopyrazoles [26][27][28] as well as on the synthesis of fused pyrazole derivatives [25]. However, a perusal of literature reveals that the importance of 5-aminopyrazoles as synthetic precursors for fused heterocycles has not been reported till now to the best of our knowledge. Recent literature shows resurgence of interest in the chemistry and bioactivity of 5-aminopyrazole derivatives leading to improvements in several already known reactions and syntheses of various fused heterocyclic derivatives with various biological activities. Considering the synthetic importance of 5-aminopyrazoles and synthesis of fused pyrazole derivatives with the need for a more general collection, herein we report an exhaustive overview of the main developments in the last decade in the chemistry of 5-aminopyrazoles for the design and synthesis of fused pyrazoloazines.The typical reactivity of 5-aminopyrazoles 5-Aminopyrazoles are polyfunctional co...

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“…Therefore, in view of the above facts and in continuation of our search on biologically active hybrid molecules [9,14], herein we report the synthesis of novel hybrid analogues (A a-h to F a-h ) with their subsequent antimycobacterial screening against Mycobacterium tuberculosis H37Rv (ATCC 27294) in BACTEC 12B medium using the microplate alamar BlueÒ assay (MABA). The above facts reveal that it is a crucial situation to fight against TB hence to develop a new therapeutic agent which is more potent than the existing drug and have a new mode of action (see Schemes 2-4).…”

Section: Introductionmentioning

confidence: 99%

“…Recognizing these serious facts, we initiated a programme to synthesize and screen diverse heterocyclic entities like pyridines, phenothiazines and pyrimidines as potential anti-tubercular agents. Based on our previous results [9,10,11,14], we set upon a programme of making antitubercular agents, using the central dihydropyrimidine as the template and adding versatile substituents on the various positions of dihydropyrimidine ring and subjected them to antimycobacterial screening.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of pyrimidinyl sulphonamide derivatives as promising class of antitubercular agents

Bhuva

Talpara

Singala

et al. 2017

Journal of Saudi Chemical Society

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A small library of compounds are synthesized and evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37RV. Two compounds, -[(2 0 ,4 0 -dinitrophenyl) sulphonyl]-4-(p-aminophenylsulphonylamino)-6-(2 0 -chlorophenyl)-pyrimidine-5-carboxamide F b and 2-hydrazino-4-(p-aminophenylsulphonylamino)-6-(2 0 -chlorophenyl)-pyrimidine-5-carboxamide D b were found to be the most active compounds in vitro with MIC of 0.02 lg/mL against MTB and were more potent compared to isoniazid (MIC: 0.03 lg/mL). ª 2015 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

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Synthesis and antimycobacterial evaluation of various 6-substituted pyrazolo[3,4-d]pyrimidine derivatives

Cited by 16 publications

References 15 publications

A review on Synthesis and Biological Evaluations of Pyrazolo[3,4-d]pyrimidine Schaffold

A review on Synthesis and Biological Evaluations of Pyrazolo[3,4-d]pyrimidine Schaffold

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

Synthesis and biological evaluation of pyrimidinyl sulphonamide derivatives as promising class of antitubercular agents

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