New Heterocyclisation Reactions of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Some 1,3-Dielectrophilic Agents

5-Amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile enters into condensation reactions with β-diketones and dibenzalacetone to form 2-(cyanomethyl)pyrazolo[1,5- a ]pyrimidine-3-carbonitrile derivatives. The reaction with cyanoguanidine in an acid medium leads to the formation of 2,4-diamino-7-(cyan...

Full description

Saved in:
Bibliographic Details
Published in:Russian journal of general chemistry 2022-03, Vol.92 (3), p.367-382
Main Authors: Semenova, A. M., Gadzhiakhmedova, Ya. R., Bespalov, A. V., Dotsenko, V. V., Aksenov, N. A., Aksenova, I. V.
Format: Article
Language:English
Subjects:
Bioavailability
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Condensates
Diketones
Proteins
Pyrazole
Pyrimidines
Quantum chemistry
Zaleplon
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c313t-8bcc14390e0ba4eb700fd1440eb27ef14f9c3311b9d2b51d363e6c11cf8818293
cites cdi_FETCH-LOGICAL-c313t-8bcc14390e0ba4eb700fd1440eb27ef14f9c3311b9d2b51d363e6c11cf8818293
container_end_page 382
container_issue 3
container_start_page 367
container_title Russian journal of general chemistry
container_volume 92
creator Semenova, A. M.
Gadzhiakhmedova, Ya. R.
Bespalov, A. V.
Dotsenko, V. V.
Aksenov, N. A.
Aksenova, I. V.
description 5-Amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile enters into condensation reactions with β-diketones and dibenzalacetone to form 2-(cyanomethyl)pyrazolo[1,5- a ]pyrimidine-3-carbonitrile derivatives. The reaction with cyanoguanidine in an acid medium leads to the formation of 2,4-diamino-7-(cyanomethyl)pyrazolo[1,5- a ][1,3,5]triazine-8-carbonitrile. Structure of the obtained compounds was confirmed by spectral data, as well as the results of a quantum chemical study of possible reaction routes for the reaction of 5-amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile with benzoyltrifluoroacetone. Bioavailability parameters were predicted for the obtained products in silico , and possible protein targets were predicted by protein-ligand docking.
doi_str_mv 10.1134/S1070363222030057
format article
fullrecord <record><control><sourceid>gale_proqu</sourceid><recordid>TN_cdi_proquest_journals_2648149900</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><galeid>A707103427</galeid><sourcerecordid>A707103427</sourcerecordid><originalsourceid>FETCH-LOGICAL-c313t-8bcc14390e0ba4eb700fd1440eb27ef14f9c3311b9d2b51d363e6c11cf8818293</originalsourceid><addsrcrecordid>eNp1kUuLFDEQgBtRcF39Ad4avCiYtSrJ9OM4rI8RFgVXz026pjKTpTsZkyxL7683wwiLqNQhBfV9VSmqql4iXCAq_e4aoQXVKCklKIBV-6g6wwY6odQKHpe8lMWx_rR6ltINAAI08qy6_8J39YYzx0ALTS6Z7IKvv7GhY5LqYOuVWM_OB6HEa1qMDzPn_TK9EbgRhyWa-zCx0IJMHIN3ObqJ6zuX9_V1IWt8q8R7xxNTjuGwd5Ojer1jn9Pz6ok1U-IXv9_z6sfHD98vN-Lq66fPl-srQQpVFt1IhFr1wDAazWMLYLeoNfAoW7aobU9KIY79Vo4r3JYluSFEsl2HnezVefXq1PcQw89bTnm4CbfRl5GDbHSHuu8BHqidmXhw3oYcDc0u0bBuoUVQWraFuvgHVWLLs6Pg2Zbt_xTwJFAMKUW2wyG62cRlQBiOlxv-ulxx5MlJhfU7jg8f_r_0C_V9l-o</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2648149900</pqid></control><display><type>article</type><title>New Heterocyclisation Reactions of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Some 1,3-Dielectrophilic Agents</title><source>Springer Nature</source><creator>Semenova, A. M. ; Gadzhiakhmedova, Ya. R. ; Bespalov, A. V. ; Dotsenko, V. V. ; Aksenov, N. A. ; Aksenova, I. V.</creator><creatorcontrib>Semenova, A. M. ; Gadzhiakhmedova, Ya. R. ; Bespalov, A. V. ; Dotsenko, V. V. ; Aksenov, N. A. ; Aksenova, I. V.</creatorcontrib><description>5-Amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile enters into condensation reactions with β-diketones and dibenzalacetone to form 2-(cyanomethyl)pyrazolo[1,5- a ]pyrimidine-3-carbonitrile derivatives. The reaction with cyanoguanidine in an acid medium leads to the formation of 2,4-diamino-7-(cyanomethyl)pyrazolo[1,5- a ][1,3,5]triazine-8-carbonitrile. Structure of the obtained compounds was confirmed by spectral data, as well as the results of a quantum chemical study of possible reaction routes for the reaction of 5-amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile with benzoyltrifluoroacetone. Bioavailability parameters were predicted for the obtained products in silico , and possible protein targets were predicted by protein-ligand docking.</description><identifier>ISSN: 1070-3632</identifier><identifier>EISSN: 1608-3350</identifier><identifier>DOI: 10.1134/S1070363222030057</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Bioavailability ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Condensates ; Diketones ; Proteins ; Pyrazole ; Pyrimidines ; Quantum chemistry ; Zaleplon</subject><ispartof>Russian journal of general chemistry, 2022-03, Vol.92 (3), p.367-382</ispartof><rights>Pleiades Publishing, Ltd. 2022</rights><rights>COPYRIGHT 2022 Springer</rights><rights>Pleiades Publishing, Ltd. 2022.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c313t-8bcc14390e0ba4eb700fd1440eb27ef14f9c3311b9d2b51d363e6c11cf8818293</citedby><cites>FETCH-LOGICAL-c313t-8bcc14390e0ba4eb700fd1440eb27ef14f9c3311b9d2b51d363e6c11cf8818293</cites><orcidid>0000-0001-8671-7608 ; 0000-0002-8083-1407 ; 0000-0003-0639-9916 ; 0000-0002-9829-9674 ; 0000-0001-7163-0497 ; 0000-0002-7125-9066</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Semenova, A. M.</creatorcontrib><creatorcontrib>Gadzhiakhmedova, Ya. R.</creatorcontrib><creatorcontrib>Bespalov, A. V.</creatorcontrib><creatorcontrib>Dotsenko, V. V.</creatorcontrib><creatorcontrib>Aksenov, N. A.</creatorcontrib><creatorcontrib>Aksenova, I. V.</creatorcontrib><title>New Heterocyclisation Reactions of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Some 1,3-Dielectrophilic Agents</title><title>Russian journal of general chemistry</title><addtitle>Russ J Gen Chem</addtitle><description>5-Amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile enters into condensation reactions with β-diketones and dibenzalacetone to form 2-(cyanomethyl)pyrazolo[1,5- a ]pyrimidine-3-carbonitrile derivatives. The reaction with cyanoguanidine in an acid medium leads to the formation of 2,4-diamino-7-(cyanomethyl)pyrazolo[1,5- a ][1,3,5]triazine-8-carbonitrile. Structure of the obtained compounds was confirmed by spectral data, as well as the results of a quantum chemical study of possible reaction routes for the reaction of 5-amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile with benzoyltrifluoroacetone. Bioavailability parameters were predicted for the obtained products in silico , and possible protein targets were predicted by protein-ligand docking.</description><subject>Bioavailability</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Condensates</subject><subject>Diketones</subject><subject>Proteins</subject><subject>Pyrazole</subject><subject>Pyrimidines</subject><subject>Quantum chemistry</subject><subject>Zaleplon</subject><issn>1070-3632</issn><issn>1608-3350</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp1kUuLFDEQgBtRcF39Ad4avCiYtSrJ9OM4rI8RFgVXz026pjKTpTsZkyxL7683wwiLqNQhBfV9VSmqql4iXCAq_e4aoQXVKCklKIBV-6g6wwY6odQKHpe8lMWx_rR6ltINAAI08qy6_8J39YYzx0ALTS6Z7IKvv7GhY5LqYOuVWM_OB6HEa1qMDzPn_TK9EbgRhyWa-zCx0IJMHIN3ObqJ6zuX9_V1IWt8q8R7xxNTjuGwd5Ojer1jn9Pz6ok1U-IXv9_z6sfHD98vN-Lq66fPl-srQQpVFt1IhFr1wDAazWMLYLeoNfAoW7aobU9KIY79Vo4r3JYluSFEsl2HnezVefXq1PcQw89bTnm4CbfRl5GDbHSHuu8BHqidmXhw3oYcDc0u0bBuoUVQWraFuvgHVWLLs6Pg2Zbt_xTwJFAMKUW2wyG62cRlQBiOlxv-ulxx5MlJhfU7jg8f_r_0C_V9l-o</recordid><startdate>20220301</startdate><enddate>20220301</enddate><creator>Semenova, A. M.</creator><creator>Gadzhiakhmedova, Ya. R.</creator><creator>Bespalov, A. V.</creator><creator>Dotsenko, V. V.</creator><creator>Aksenov, N. A.</creator><creator>Aksenova, I. V.</creator><general>Pleiades Publishing</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-8671-7608</orcidid><orcidid>https://orcid.org/0000-0002-8083-1407</orcidid><orcidid>https://orcid.org/0000-0003-0639-9916</orcidid><orcidid>https://orcid.org/0000-0002-9829-9674</orcidid><orcidid>https://orcid.org/0000-0001-7163-0497</orcidid><orcidid>https://orcid.org/0000-0002-7125-9066</orcidid></search><sort><creationdate>20220301</creationdate><title>New Heterocyclisation Reactions of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Some 1,3-Dielectrophilic Agents</title><author>Semenova, A. M. ; Gadzhiakhmedova, Ya. R. ; Bespalov, A. V. ; Dotsenko, V. V. ; Aksenov, N. A. ; Aksenova, I. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c313t-8bcc14390e0ba4eb700fd1440eb27ef14f9c3311b9d2b51d363e6c11cf8818293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Bioavailability</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Condensates</topic><topic>Diketones</topic><topic>Proteins</topic><topic>Pyrazole</topic><topic>Pyrimidines</topic><topic>Quantum chemistry</topic><topic>Zaleplon</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Semenova, A. M.</creatorcontrib><creatorcontrib>Gadzhiakhmedova, Ya. R.</creatorcontrib><creatorcontrib>Bespalov, A. V.</creatorcontrib><creatorcontrib>Dotsenko, V. V.</creatorcontrib><creatorcontrib>Aksenov, N. A.</creatorcontrib><creatorcontrib>Aksenova, I. V.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of general chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Semenova, A. M.</au><au>Gadzhiakhmedova, Ya. R.</au><au>Bespalov, A. V.</au><au>Dotsenko, V. V.</au><au>Aksenov, N. A.</au><au>Aksenova, I. V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Heterocyclisation Reactions of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Some 1,3-Dielectrophilic Agents</atitle><jtitle>Russian journal of general chemistry</jtitle><stitle>Russ J Gen Chem</stitle><date>2022-03-01</date><risdate>2022</risdate><volume>92</volume><issue>3</issue><spage>367</spage><epage>382</epage><pages>367-382</pages><issn>1070-3632</issn><eissn>1608-3350</eissn><abstract>5-Amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile enters into condensation reactions with β-diketones and dibenzalacetone to form 2-(cyanomethyl)pyrazolo[1,5- a ]pyrimidine-3-carbonitrile derivatives. The reaction with cyanoguanidine in an acid medium leads to the formation of 2,4-diamino-7-(cyanomethyl)pyrazolo[1,5- a ][1,3,5]triazine-8-carbonitrile. Structure of the obtained compounds was confirmed by spectral data, as well as the results of a quantum chemical study of possible reaction routes for the reaction of 5-amino-3-(cyanomethyl)-1 H -pyrazole-4-carbonitrile with benzoyltrifluoroacetone. Bioavailability parameters were predicted for the obtained products in silico , and possible protein targets were predicted by protein-ligand docking.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1070363222030057</doi><tpages>16</tpages><orcidid>https://orcid.org/0000-0001-8671-7608</orcidid><orcidid>https://orcid.org/0000-0002-8083-1407</orcidid><orcidid>https://orcid.org/0000-0003-0639-9916</orcidid><orcidid>https://orcid.org/0000-0002-9829-9674</orcidid><orcidid>https://orcid.org/0000-0001-7163-0497</orcidid><orcidid>https://orcid.org/0000-0002-7125-9066</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1070-3632
ispartof Russian journal of general chemistry, 2022-03, Vol.92 (3), p.367-382
issn 1070-3632
1608-3350
language eng
recordid cdi_proquest_journals_2648149900
source Springer Nature
subjects Bioavailability
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Condensates
Diketones
Proteins
Pyrazole
Pyrimidines
Quantum chemistry
Zaleplon
title New Heterocyclisation Reactions of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Some 1,3-Dielectrophilic Agents
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T13%3A25%3A49IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-gale_proqu&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=New%20Heterocyclisation%20Reactions%20of%205-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile%20with%20Some%201,3-Dielectrophilic%20Agents&rft.jtitle=Russian%20journal%20of%20general%20chemistry&rft.au=Semenova,%20A.%20M.&rft.date=2022-03-01&rft.volume=92&rft.issue=3&rft.spage=367&rft.epage=382&rft.pages=367-382&rft.issn=1070-3632&rft.eissn=1608-3350&rft_id=info:doi/10.1134/S1070363222030057&rft_dat=%3Cgale_proqu%3EA707103427%3C/gale_proqu%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c313t-8bcc14390e0ba4eb700fd1440eb27ef14f9c3311b9d2b51d363e6c11cf8818293%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2648149900&rft_id=info:pmid/&rft_galeid=A707103427&rfr_iscdi=true