Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents

Bantwal Shivarama Holla, Manjathuru Mahalinga, Mari Sitambaram Karthikeyan, Padiyath Mohamed Akberali, Nalilu Sucheta Shetty

Research output: Contribution to journalArticle

191 Citations (Scopus)

Abstract

The reaction of 4-hydrazino-8-(trifluoromethyl)quinoline (2) with ethoxymethylenecyanoacetate afforded ethyl 5-amino-1-[8-(trifluoromethyl) quinolin-4-yl]-1H-pyrazole-4-carboxylate (3) and that with ethoxymethylenemalononitrile afforded 5-amino-1-[8-(trifluoromethyl)quinolin-4- yl]-1H-pyrazole-4-carbonitrile (5). Compounds 3 and 5 were hydrolyzed to get 5-amino-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-pyrazole-4-carboxylic acid and then reacted with acetic anhydride to afford 6-methyl-1-[8-(trifluoromethyl) quinolin-4-yl]pyrazolo[3,4-d]oxazin-4-one (6), which was condensed with different aromatic amines to give a series of 5-substituted 6-methyl-1-[8- (trifluoromethyl)quinolin-4-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-ones (7). Compounds 3 and 5 also reacted with formamide, urea, and thiourea affording the corresponding pyrazolo[3,4-d]pyrimidines (8-13), respectively. Structures of the products have been determined by chemical reactions and spectral studies. All compounds of the series have been screened for their antibacterial and antifungal activity studies. The results are summarized in Tables 1 and 2.

Original languageEnglish
Pages (from-to)2040-2047
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume14
Issue number6
DOIs
Publication statusPublished - 15-03-2006
Externally publishedYes

Fingerprint

pyrazolo(3,4-d)pyrimidine
Anti-Infective Agents
Derivatives
Thiourea
Allopurinol
Carboxylic Acids
Amines
Urea
Chemical reactions
pyrazole

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Holla, Bantwal Shivarama ; Mahalinga, Manjathuru ; Karthikeyan, Mari Sitambaram ; Akberali, Padiyath Mohamed ; Shetty, Nalilu Sucheta. / Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents. In: Bioorganic and Medicinal Chemistry. 2006 ; Vol. 14, No. 6. pp. 2040-2047.
@article{69168801d36e4c3bba510bf1c2ed299c,
title = "Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents",
abstract = "The reaction of 4-hydrazino-8-(trifluoromethyl)quinoline (2) with ethoxymethylenecyanoacetate afforded ethyl 5-amino-1-[8-(trifluoromethyl) quinolin-4-yl]-1H-pyrazole-4-carboxylate (3) and that with ethoxymethylenemalononitrile afforded 5-amino-1-[8-(trifluoromethyl)quinolin-4- yl]-1H-pyrazole-4-carbonitrile (5). Compounds 3 and 5 were hydrolyzed to get 5-amino-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-pyrazole-4-carboxylic acid and then reacted with acetic anhydride to afford 6-methyl-1-[8-(trifluoromethyl) quinolin-4-yl]pyrazolo[3,4-d]oxazin-4-one (6), which was condensed with different aromatic amines to give a series of 5-substituted 6-methyl-1-[8- (trifluoromethyl)quinolin-4-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-ones (7). Compounds 3 and 5 also reacted with formamide, urea, and thiourea affording the corresponding pyrazolo[3,4-d]pyrimidines (8-13), respectively. Structures of the products have been determined by chemical reactions and spectral studies. All compounds of the series have been screened for their antibacterial and antifungal activity studies. The results are summarized in Tables 1 and 2.",
author = "Holla, {Bantwal Shivarama} and Manjathuru Mahalinga and Karthikeyan, {Mari Sitambaram} and Akberali, {Padiyath Mohamed} and Shetty, {Nalilu Sucheta}",
year = "2006",
month = "3",
day = "15",
doi = "10.1016/j.bmc.2005.10.053",
language = "English",
volume = "14",
pages = "2040--2047",
journal = "Bioorganic and Medicinal Chemistry",
issn = "0968-0896",
publisher = "Elsevier Ireland Ltd",
number = "6",

}

Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents. / Holla, Bantwal Shivarama; Mahalinga, Manjathuru; Karthikeyan, Mari Sitambaram; Akberali, Padiyath Mohamed; Shetty, Nalilu Sucheta.

In: Bioorganic and Medicinal Chemistry, Vol. 14, No. 6, 15.03.2006, p. 2040-2047.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents

AU - Holla, Bantwal Shivarama

AU - Mahalinga, Manjathuru

AU - Karthikeyan, Mari Sitambaram

AU - Akberali, Padiyath Mohamed

AU - Shetty, Nalilu Sucheta

PY - 2006/3/15

Y1 - 2006/3/15

N2 - The reaction of 4-hydrazino-8-(trifluoromethyl)quinoline (2) with ethoxymethylenecyanoacetate afforded ethyl 5-amino-1-[8-(trifluoromethyl) quinolin-4-yl]-1H-pyrazole-4-carboxylate (3) and that with ethoxymethylenemalononitrile afforded 5-amino-1-[8-(trifluoromethyl)quinolin-4- yl]-1H-pyrazole-4-carbonitrile (5). Compounds 3 and 5 were hydrolyzed to get 5-amino-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-pyrazole-4-carboxylic acid and then reacted with acetic anhydride to afford 6-methyl-1-[8-(trifluoromethyl) quinolin-4-yl]pyrazolo[3,4-d]oxazin-4-one (6), which was condensed with different aromatic amines to give a series of 5-substituted 6-methyl-1-[8- (trifluoromethyl)quinolin-4-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-ones (7). Compounds 3 and 5 also reacted with formamide, urea, and thiourea affording the corresponding pyrazolo[3,4-d]pyrimidines (8-13), respectively. Structures of the products have been determined by chemical reactions and spectral studies. All compounds of the series have been screened for their antibacterial and antifungal activity studies. The results are summarized in Tables 1 and 2.

AB - The reaction of 4-hydrazino-8-(trifluoromethyl)quinoline (2) with ethoxymethylenecyanoacetate afforded ethyl 5-amino-1-[8-(trifluoromethyl) quinolin-4-yl]-1H-pyrazole-4-carboxylate (3) and that with ethoxymethylenemalononitrile afforded 5-amino-1-[8-(trifluoromethyl)quinolin-4- yl]-1H-pyrazole-4-carbonitrile (5). Compounds 3 and 5 were hydrolyzed to get 5-amino-1-[8-(trifluoromethyl)quinolin-4-yl]-1H-pyrazole-4-carboxylic acid and then reacted with acetic anhydride to afford 6-methyl-1-[8-(trifluoromethyl) quinolin-4-yl]pyrazolo[3,4-d]oxazin-4-one (6), which was condensed with different aromatic amines to give a series of 5-substituted 6-methyl-1-[8- (trifluoromethyl)quinolin-4-yl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-ones (7). Compounds 3 and 5 also reacted with formamide, urea, and thiourea affording the corresponding pyrazolo[3,4-d]pyrimidines (8-13), respectively. Structures of the products have been determined by chemical reactions and spectral studies. All compounds of the series have been screened for their antibacterial and antifungal activity studies. The results are summarized in Tables 1 and 2.

UR - http://www.scopus.com/inward/record.url?scp=32044468685&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=32044468685&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2005.10.053

DO - 10.1016/j.bmc.2005.10.053

M3 - Article

VL - 14

SP - 2040

EP - 2047

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

IS - 6

ER -