Synthesis of 7H‐tetrazolo[1,5‐c]pyrrolo[3,2‐e]pyrimidines and their reductive ring cleavage to 4‐aminopyrrolo[2,3‐d]pyrimidines

Dave, Chaitanya G.; Shah, Rina D.

doi:10.1002/jhet.5570350609

Cited by 37 publications

(37 citation statements)

References 11 publications

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“…Compound 12 was converted, in the presence of hydrochloric acid, into 2,4-diamino-5-oxo-5H-benzo [5,6] …”

Section: Methodsmentioning

confidence: 99%

“…[1][2][3][4][5][6][7] A series of 1,6-naphthyridines have been demonstrated as anti-human cytomegalovirus (HCMV) activity. [8][9][10][11] Furthermore, chromenes and their fused heterocyclic derivatives have attracted a great deal of interest due to their wide applications in the field of pharmaceuticals.…”

Section: Introductionmentioning

confidence: 99%

“…[8][9][10][11] Furthermore, chromenes and their fused heterocyclic derivatives have attracted a great deal of interest due to their wide applications in the field of pharmaceuticals. [12][13][14][15][16][17] In view of the above mentioned benefits and in continuation of our previous work in developing syntheses of polyfunctionally substituted heterocyclic compounds with potential biological activity, [18][19][20][21][22][23][24][25][26][27] we report here the utility of the 2-(3-amino-2-cyano-1H-benzo[f]chromen-1-yl)-malononitrile (1) as a building block for the synthesis of benzo [5,6]chromeno [4,3,2-de] [1,6]naphthyridines and benzo [5,6]chromeno [3,4-c]pyridine with the purpose of investigating in the future their possible biological activity.…”

Section: Introductionmentioning

confidence: 99%

“…

AbstractCyclocondensation of 2-(3-amino-2-cyano-1H-benzo[f]chromen-1-yl)-malononitrile (1) with β-dicarbonyles 2a-d, benzoylacetonitrile 2e, malononitrile 2f, and 3-aminocrotononitrile (9) gave the benzo [5,6]

…”

mentioning

confidence: 99%

“…As described in Scheme 2, the 2-amino-5-methyl-benzo [5,6]chromeno[4,3,2-de]- [1,6]naphthyridine-1,4-dicarbonitrile (11) was obtained when 1 was heated under reflux with 3-amino-crotononitrile (9) in boiling ethanol. Depending upon the spectroscopic data the structure of compound 11 is undoubtedly confirmed.…”

mentioning

confidence: 99%

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Synthesis of polyfunctionally substituted benzo[5,6]chromeno[4,3,2-de][1,6]naphthyridines and 5H-benzo[5,6]chromeno[3,4-c]pyridines

Shaker¹

2006

Arkivoc

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“…Compound 12 was converted, in the presence of hydrochloric acid, into 2,4-diamino-5-oxo-5H-benzo [5,6] …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…

…”

mentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis of polyfunctionally substituted benzo[5,6]chromeno[4,3,2-de][1,6]naphthyridines and 5H-benzo[5,6]chromeno[3,4-c]pyridines

Shaker¹

2006

Arkivoc

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Pyrido [2, 3-d]pyrimidines and Pyrimido[5′, 4′:5, 6]pyrido[2, 3-d]pyrimidines as New Antiviral Agents: Synthesis and Biological Activity

Nasr

Gineinah

2002

Arch. Pharm. Pharm. Med. Chem.

213

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A series of 7‐amino‐ and 7‐oxo‐5‐aryl‐6‐cyanopyrido[2, 3‐d]pyrimidines, 4 and 11, respectively, and pyrimido [5′, 4′:5, 6]pyrido[2, 3‐d]pyrimidine derivatives 6 and 7 was synthesized and investigated as antiviral agents. Different synthetic strategies for the preparation of the target compounds were explored. A synthetic procedure for 4 and 11 starting with 6‐amino‐1, 2, 3, 4‐tetrahydro‐2, 4‐dioxopyrimidine, proper aldehyde, and malononitrile or ethyl cyanoacetate, respectively, in a one‐pot reaction proved to be the method of choice for preparation of compounds of such type. Construction of another pyrimidine ring on the pyridine nucleus of compound 4 was achieved either by reaction with phenyl iso(thio)cyanate or with formic acid to yield 6 and 7, respectively. The structure of the prepared compounds was confirmed through elemental analysis and spectral investigation. Most of the newly synthesized compounds were subjected to antiviral activity testing against herpes simplex virus (HSV) where some of them show good activities.

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Synthesis and biological evaluation of some new tricyclic pyrrolo[3,2‐e]tetrazolo[1,5‐c]pyrimidine derivatives as potential antitubercular agents

Patil¹,

Shingare²,

Choudhari

et al. 2018

Archiv der Pharmazie

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A series of new tricyclic pyrrolo[3,2-e]tetrazolo[1,5-c]pyrimidines 8a-l were synthesized and characterized by IR, NMR ( H and C), and mass spectral analysis. The newly synthesized compounds 8a-l were inspected for their in vitro antitubercular activity against Mycobacterium tuberculosis (MTB) H Ra using an established XTT reduction menadione assay (XRMA). The title compounds exhibited minimum inhibitory concentrations (MIC ) ranging from 0.09 to >30 μg/mL. Five compounds (8c, 8i-l) were further confirmed for their dose-dependent effect against MTB. These compounds were evaluated in the THP-1 infection model, where 8i (MIC = 0.35 μg/mL), 8j (MIC = 1.17 μg/mL), 8k (MIC = 2.38 μg/mL), and 8l (MIC = 1.17 μg/mL) demonstrated significant antitubercular activity. All the ex vivo active compounds showed insignificant cytotoxicity against the human cancer cell lines, HeLa, MCF-7, and THP-1. Inactivity of all these compounds against Gram positive and Gram negative bacteria indicates their specificity. Molecular docking studies in the active site of the sterol 14alpha-demethylase (CYP51) enzyme revealed a similar binding mode to the native ligand in the crystal structure, thereby helping to understand the ligand-protein interactions and to establish a structural basis for inhibition of MTB. The results suggest novel pharmacophores as selective and specific inhibitors against MTB that can be explored further to synthesize lead compounds against tuberculosis. In summary, the results clearly indicate the identification of some novel, selective, and specific inhibitors against MTB that can be explored further for potential antitubercular drugs.

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Synthesis of 7H‐tetrazolo[1,5‐c]pyrrolo[3,2‐e]pyrimidines and their reductive ring cleavage to 4‐aminopyrrolo[2,3‐d]pyrimidines

Cited by 37 publications

References 11 publications

Synthesis of polyfunctionally substituted benzo[5,6]chromeno[4,3,2-de][1,6]naphthyridines and 5H-benzo[5,6]chromeno[3,4-c]pyridines

Synthesis of polyfunctionally substituted benzo[5,6]chromeno[4,3,2-de][1,6]naphthyridines and 5H-benzo[5,6]chromeno[3,4-c]pyridines

Pyrido [2, 3-d]pyrimidines and Pyrimido[5′, 4′:5, 6]pyrido[2, 3-d]pyrimidines as New Antiviral Agents: Synthesis and Biological Activity

Synthesis and biological evaluation of some new tricyclic pyrrolo[3,2‐e]tetrazolo[1,5‐c]pyrimidine derivatives as potential antitubercular agents

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