Convenient synthesis of novel 4-substitutedamino-5-trifluoromethyl–2,7-disubstituted pyrido[2,3- d] pyrimidines and their antibacterial activity

Novel pyrido[2,3- d]pyrimidines 4 have been synthesised starting from 2-amino-4-trifluoromethyl-6-substituted nicotinonitriles 1 via imine formation, selective amination followed by Dimroth rearrangement. Compound 4 were screened against Gram +ve and –ve bacteria in vitro. Compounds 4h and 4d showed...

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Veröffentlicht in:	European journal of medicinal chemistry 2006-08, Vol.41 (8), p.1011-1016
Hauptverfasser:	Ravi Kanth, S., Venkat Reddy, G., Hara Kishore, K., Shanthan Rao, P., Narsaiah, B., Surya Narayana Murthy, U.
Format:	Artikel
Sprache:	eng
Schlagworte:	Aminolysis Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - pharmacology Antibacterial Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Biological and medical sciences Ciprofloxacin Dimroth rearrangement Gram-Negative Bacteria - drug effects Gram-Positive Bacteria - drug effects Imino-ether Magnetic Resonance Spectroscopy Medical sciences Microbial Sensitivity Tests Pharmacology. Drug treatments Pyrido[2,3- d]pyrimidines Pyrimidines - chemical synthesis Pyrimidines - pharmacology Spectrometry, Mass, Electrospray Ionization Spectrophotometry, Infrared
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container_end_page	1016
container_issue	8
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container_title	European journal of medicinal chemistry
container_volume	41
creator	Ravi Kanth, S. Venkat Reddy, G. Hara Kishore, K. Shanthan Rao, P. Narsaiah, B. Surya Narayana Murthy, U.
description	Novel pyrido[2,3- d]pyrimidines 4 have been synthesised starting from 2-amino-4-trifluoromethyl-6-substituted nicotinonitriles 1 via imine formation, selective amination followed by Dimroth rearrangement. Compound 4 were screened against Gram +ve and –ve bacteria in vitro. Compounds 4h and 4d showed significant activity against all species of Gram positive bacteria and moderate activity against Gram negative bacteria. N-2,4 difluorophenyl compounds 4l and 4m were the least active among all the compounds. All the compounds were inactive against Pseudomonas aeruginosa at the maximum concentration of 200 μg ml –1. Novel pyrido[2,3- d]pyrimidines 4 have been synthesised starting from 2-amino-4-trifluoromethyl-6-substituted nicotinonitriles 1 via imine formation, selective amination followed by Dimroth rearrangement. Compounds 4 were screened against Gram +ve and –ve bacteria in vitro. Compounds 4h and 4d showed significant activity against all species of Gram positive bacteria and moderate activity against Gram negative bacteria. N-2,4 difluorophenyl compounds 4l and 4m were the least active among all the compounds. All the compounds were inactive against Pseudomonas aeruginosa at the maximum concentration of 200 μg ml –1.
doi_str_mv	10.1016/j.ejmech.2006.03.028
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Compound 4 were screened against Gram +ve and –ve bacteria in vitro. Compounds 4h and 4d showed significant activity against all species of Gram positive bacteria and moderate activity against Gram negative bacteria. N-2,4 difluorophenyl compounds 4l and 4m were the least active among all the compounds. All the compounds were inactive against Pseudomonas aeruginosa at the maximum concentration of 200 μg ml –1. Novel pyrido[2,3- d]pyrimidines 4 have been synthesised starting from 2-amino-4-trifluoromethyl-6-substituted nicotinonitriles 1 via imine formation, selective amination followed by Dimroth rearrangement. Compounds 4 were screened against Gram +ve and –ve bacteria in vitro. Compounds 4h and 4d showed significant activity against all species of Gram positive bacteria and moderate activity against Gram negative bacteria. N-2,4 difluorophenyl compounds 4l and 4m were the least active among all the compounds. 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Compound 4 were screened against Gram +ve and –ve bacteria in vitro. Compounds 4h and 4d showed significant activity against all species of Gram positive bacteria and moderate activity against Gram negative bacteria. N-2,4 difluorophenyl compounds 4l and 4m were the least active among all the compounds. All the compounds were inactive against Pseudomonas aeruginosa at the maximum concentration of 200 μg ml –1. Novel pyrido[2,3- d]pyrimidines 4 have been synthesised starting from 2-amino-4-trifluoromethyl-6-substituted nicotinonitriles 1 via imine formation, selective amination followed by Dimroth rearrangement. Compounds 4 were screened against Gram +ve and –ve bacteria in vitro. Compounds 4h and 4d showed significant activity against all species of Gram positive bacteria and moderate activity against Gram negative bacteria. N-2,4 difluorophenyl compounds 4l and 4m were the least active among all the compounds. All the compounds were inactive against Pseudomonas aeruginosa at the maximum concentration of 200 μg ml –1.</description><subject>Aminolysis</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Biological and medical sciences</subject><subject>Ciprofloxacin</subject><subject>Dimroth rearrangement</subject><subject>Gram-Negative Bacteria - drug effects</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>Imino-ether</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrido[2,3- d]pyrimidines</subject><subject>Pyrimidines - chemical synthesis</subject><subject>Pyrimidines - pharmacology</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Spectrophotometry, Infrared</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kcuKFDEUhoMoTjv6BiK10dVUmUtVqmojDM2MCgNudCUScjlFp6lK2iTVUDvfQdz3s_Sj-CRm7IZx5SoJfOfk_OdD6CXBFcGEv91WsJ1AbyqKMa8wqzDtHqEVaXlXMtrUj9EKU8rKhrL6Aj2LcYsxbjjGT9EF4S3nuOtW6Nfauz04Cy4VcXFpA9HGwg_Hg_N7GIu6jLOKyaY5gZGTdb5syhTsMM4--AnSZhl___hJr9rS2H_QYrcEa_xXesXKwnz7-5yssQ5iIZ05HvJPNhwP0iWrpE4QrByLfLF7m5bn6Mkgxwgvzucl-nJ783n9obz79P7j-vqu1DlgytEUNP1QD4PUDdABaoappq0iSvWGKtLxFvpa9w2H3vAB09ZowtpeKSAdNuwSvTn13QX_fYaYxGSjhnGUDvwcBe-6hjWYZbA-gTr4GAMMYpfzyLAIgsW9DrEVJx3iXofATGQduezVuf-sJjAPRef9Z-D1GZBRy3EI0mkbH7gOM56jZu7diYO8jb2FIKLOzjQYG0AnYbz9_yR_AIvfsgM</recordid><startdate>200608</startdate><enddate>200608</enddate><creator>Ravi Kanth, S.</creator><creator>Venkat Reddy, G.</creator><creator>Hara Kishore, K.</creator><creator>Shanthan Rao, P.</creator><creator>Narsaiah, B.</creator><creator>Surya Narayana Murthy, U.</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>200608</creationdate><title>Convenient synthesis of novel 4-substitutedamino-5-trifluoromethyl–2,7-disubstituted pyrido[2,3- d] pyrimidines and their antibacterial activity</title><author>Ravi Kanth, S. ; Venkat Reddy, G. ; Hara Kishore, K. ; Shanthan Rao, P. ; Narsaiah, B. ; Surya Narayana Murthy, U.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c254t-52be59f4ffac5e2fe4302c27b1bb9d2b1867e94c956e9d6f027dc1379bbe180d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Aminolysis</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Biological and medical sciences</topic><topic>Ciprofloxacin</topic><topic>Dimroth rearrangement</topic><topic>Gram-Negative Bacteria - drug effects</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>Imino-ether</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrido[2,3- d]pyrimidines</topic><topic>Pyrimidines - chemical synthesis</topic><topic>Pyrimidines - pharmacology</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Spectrophotometry, Infrared</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ravi Kanth, S.</creatorcontrib><creatorcontrib>Venkat Reddy, G.</creatorcontrib><creatorcontrib>Hara Kishore, K.</creatorcontrib><creatorcontrib>Shanthan Rao, P.</creatorcontrib><creatorcontrib>Narsaiah, B.</creatorcontrib><creatorcontrib>Surya Narayana Murthy, U.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ravi Kanth, S.</au><au>Venkat Reddy, G.</au><au>Hara Kishore, K.</au><au>Shanthan Rao, P.</au><au>Narsaiah, B.</au><au>Surya Narayana Murthy, U.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Convenient synthesis of novel 4-substitutedamino-5-trifluoromethyl–2,7-disubstituted pyrido[2,3- d] pyrimidines and their antibacterial activity</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2006-08</date><risdate>2006</risdate><volume>41</volume><issue>8</issue><spage>1011</spage><epage>1016</epage><pages>1011-1016</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Novel pyrido[2,3- d]pyrimidines 4 have been synthesised starting from 2-amino-4-trifluoromethyl-6-substituted nicotinonitriles 1 via imine formation, selective amination followed by Dimroth rearrangement. Compound 4 were screened against Gram +ve and –ve bacteria in vitro. Compounds 4h and 4d showed significant activity against all species of Gram positive bacteria and moderate activity against Gram negative bacteria. N-2,4 difluorophenyl compounds 4l and 4m were the least active among all the compounds. All the compounds were inactive against Pseudomonas aeruginosa at the maximum concentration of 200 μg ml –1. Novel pyrido[2,3- d]pyrimidines 4 have been synthesised starting from 2-amino-4-trifluoromethyl-6-substituted nicotinonitriles 1 via imine formation, selective amination followed by Dimroth rearrangement. Compounds 4 were screened against Gram +ve and –ve bacteria in vitro. Compounds 4h and 4d showed significant activity against all species of Gram positive bacteria and moderate activity against Gram negative bacteria. N-2,4 difluorophenyl compounds 4l and 4m were the least active among all the compounds. All the compounds were inactive against Pseudomonas aeruginosa at the maximum concentration of 200 μg ml –1.</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>16766088</pmid><doi>10.1016/j.ejmech.2006.03.028</doi><tpages>6</tpages></addata></record>
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source	MEDLINE; Elsevier ScienceDirect Journals
subjects	Aminolysis Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - pharmacology Antibacterial Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Biological and medical sciences Ciprofloxacin Dimroth rearrangement Gram-Negative Bacteria - drug effects Gram-Positive Bacteria - drug effects Imino-ether Magnetic Resonance Spectroscopy Medical sciences Microbial Sensitivity Tests Pharmacology. Drug treatments Pyrido[2,3- d]pyrimidines Pyrimidines - chemical synthesis Pyrimidines - pharmacology Spectrometry, Mass, Electrospray Ionization Spectrophotometry, Infrared
title	Convenient synthesis of novel 4-substitutedamino-5-trifluoromethyl–2,7-disubstituted pyrido[2,3- d] pyrimidines and their antibacterial activity
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