Synthesis and Biological Activity of 5-alkoxy- and 5-amino-substituted 3-bromo-4-nitro-1-(thietan-3-yl)-1H-pyrazoles
5-Alkoxy- and 5-amino-substituted 3-bromo-4-nitro-1-(thietan-3-yl)-1 H -pyrazoles were synthesized by reactions of 3,5-dibromo-4-nitro-1-(thietan-3-yl)-1 H -pyrazole with sodium alcoholates and primary amines. The structures of the synthesized compounds were established by IR, PMR, and 13 C NMR spec...
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| Veröffentlicht in: | Pharmaceutical chemistry journal 2022-06, Vol.56 (3), p.316-320 |
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| creator | Khaliullin, F. A. Klen, E. E. Pavlov, V. N. Samorodov, A. V. Shepilova, S. O. Makarova, N. N. Nurlanova, S. N. Abzalilov, T. N. |
| description | 5-Alkoxy- and 5-amino-substituted 3-bromo-4-nitro-1-(thietan-3-yl)-1
H
-pyrazoles were synthesized by reactions of 3,5-dibromo-4-nitro-1-(thietan-3-yl)-1
H
-pyrazole with sodium alcoholates and primary amines. The structures of the synthesized compounds were established by IR, PMR, and
13
C NMR spectroscopy.
In vitro
studies of the antiplatelet, anticoagulant, and antioxidant activity revealed promising compounds, including 3-bromo-5-methoxy-4-nitro-1-(thietan-3-yl)-1
H
-pyrazole with antioxidant action and 2-{[3-bromo-4-nitro-1-(thietan-3-yl)-1
H
-pyrazol-5-yl]amino}ethan-1-ol with an antiplatelet effect. Results of
in silico
calculations predicted the absence of toxic risks (mutagenicity, oncogenicity, reproductive toxicity, local irritation) and acceptable bioavailability (in terms of the topological polar surface area). |
| doi_str_mv | 10.1007/s11094-022-02636-9 |
| format | Article |
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H
-pyrazoles were synthesized by reactions of 3,5-dibromo-4-nitro-1-(thietan-3-yl)-1
H
-pyrazole with sodium alcoholates and primary amines. The structures of the synthesized compounds were established by IR, PMR, and
13
C NMR spectroscopy.
In vitro
studies of the antiplatelet, anticoagulant, and antioxidant activity revealed promising compounds, including 3-bromo-5-methoxy-4-nitro-1-(thietan-3-yl)-1
H
-pyrazole with antioxidant action and 2-{[3-bromo-4-nitro-1-(thietan-3-yl)-1
H
-pyrazol-5-yl]amino}ethan-1-ol with an antiplatelet effect. Results of
in silico
calculations predicted the absence of toxic risks (mutagenicity, oncogenicity, reproductive toxicity, local irritation) and acceptable bioavailability (in terms of the topological polar surface area).</description><identifier>ISSN: 0091-150X</identifier><identifier>EISSN: 1573-9031</identifier><identifier>DOI: 10.1007/s11094-022-02636-9</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Anticoagulants (Medicine) ; Antioxidants ; Medicine ; Nuclear magnetic resonance spectroscopy ; Organic Chemistry ; Pharmacology/Toxicology ; Pharmacy</subject><ispartof>Pharmaceutical chemistry journal, 2022-06, Vol.56 (3), p.316-320</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2022</rights><rights>COPYRIGHT 2022 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c358t-da9bff8a1f9ec3be2a7f2c084c2bb5c56d61d8697e182aaf79b8487451a2331e3</citedby><cites>FETCH-LOGICAL-c358t-da9bff8a1f9ec3be2a7f2c084c2bb5c56d61d8697e182aaf79b8487451a2331e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11094-022-02636-9$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11094-022-02636-9$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>315,781,785,27929,27930,41493,42562,51324</link.rule.ids></links><search><creatorcontrib>Khaliullin, F. A.</creatorcontrib><creatorcontrib>Klen, E. E.</creatorcontrib><creatorcontrib>Pavlov, V. N.</creatorcontrib><creatorcontrib>Samorodov, A. V.</creatorcontrib><creatorcontrib>Shepilova, S. O.</creatorcontrib><creatorcontrib>Makarova, N. N.</creatorcontrib><creatorcontrib>Nurlanova, S. N.</creatorcontrib><creatorcontrib>Abzalilov, T. N.</creatorcontrib><title>Synthesis and Biological Activity of 5-alkoxy- and 5-amino-substituted 3-bromo-4-nitro-1-(thietan-3-yl)-1H-pyrazoles</title><title>Pharmaceutical chemistry journal</title><addtitle>Pharm Chem J</addtitle><description>5-Alkoxy- and 5-amino-substituted 3-bromo-4-nitro-1-(thietan-3-yl)-1
H
-pyrazoles were synthesized by reactions of 3,5-dibromo-4-nitro-1-(thietan-3-yl)-1
H
-pyrazole with sodium alcoholates and primary amines. The structures of the synthesized compounds were established by IR, PMR, and
13
C NMR spectroscopy.
In vitro
studies of the antiplatelet, anticoagulant, and antioxidant activity revealed promising compounds, including 3-bromo-5-methoxy-4-nitro-1-(thietan-3-yl)-1
H
-pyrazole with antioxidant action and 2-{[3-bromo-4-nitro-1-(thietan-3-yl)-1
H
-pyrazol-5-yl]amino}ethan-1-ol with an antiplatelet effect. Results of
in silico
calculations predicted the absence of toxic risks (mutagenicity, oncogenicity, reproductive toxicity, local irritation) and acceptable bioavailability (in terms of the topological polar surface area).</description><subject>Anticoagulants (Medicine)</subject><subject>Antioxidants</subject><subject>Medicine</subject><subject>Nuclear magnetic resonance spectroscopy</subject><subject>Organic Chemistry</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><issn>0091-150X</issn><issn>1573-9031</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kclKBDEQhoMoOC4v4KnBix5qzNJbjqO4geBBBW8hnU7GaHciSUZsn97oeBFEiqJI-L6C4kfogOA5wbg5iYRgXgKmNHfNauAbaEaqhgHHjGyiGcacAKnw4zbaifEZ46wxOkPpbnLpSUcbC-n64tT6wS-tkkOxUMm-2TQV3hQVyOHFv0_wDeXXaJ2HuOpismmVdF8w6IIfPZTgbAoeCBylJ6uTdMBgGo6BXMHrFOSHH3TcQ1tGDlHv_8xd9HBxfn92BTe3l9dnixtQrGoT9JJ3xrSSGK4V6zSVjaEKt6WiXVepqu5r0rc1bzRpqZSm4V1btk1ZEUkZI5rtosP13qUctLDO-BSkGm1UYtHguuFtVdaZmv9B5er1aJV32tj8_0uga0EFH2PQRrwGO8owCYLFVxxiHYfIcYjvOATPEltLMcNuqYN49qvg8vn_WZ__k4xd</recordid><startdate>20220601</startdate><enddate>20220601</enddate><creator>Khaliullin, F. A.</creator><creator>Klen, E. E.</creator><creator>Pavlov, V. N.</creator><creator>Samorodov, A. V.</creator><creator>Shepilova, S. O.</creator><creator>Makarova, N. N.</creator><creator>Nurlanova, S. N.</creator><creator>Abzalilov, T. N.</creator><general>Springer US</general><general>Springer</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20220601</creationdate><title>Synthesis and Biological Activity of 5-alkoxy- and 5-amino-substituted 3-bromo-4-nitro-1-(thietan-3-yl)-1H-pyrazoles</title><author>Khaliullin, F. A. ; Klen, E. E. ; Pavlov, V. N. ; Samorodov, A. V. ; Shepilova, S. O. ; Makarova, N. N. ; Nurlanova, S. N. ; Abzalilov, T. N.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c358t-da9bff8a1f9ec3be2a7f2c084c2bb5c56d61d8697e182aaf79b8487451a2331e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Anticoagulants (Medicine)</topic><topic>Antioxidants</topic><topic>Medicine</topic><topic>Nuclear magnetic resonance spectroscopy</topic><topic>Organic Chemistry</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Khaliullin, F. A.</creatorcontrib><creatorcontrib>Klen, E. E.</creatorcontrib><creatorcontrib>Pavlov, V. N.</creatorcontrib><creatorcontrib>Samorodov, A. V.</creatorcontrib><creatorcontrib>Shepilova, S. O.</creatorcontrib><creatorcontrib>Makarova, N. N.</creatorcontrib><creatorcontrib>Nurlanova, S. N.</creatorcontrib><creatorcontrib>Abzalilov, T. N.</creatorcontrib><collection>CrossRef</collection><jtitle>Pharmaceutical chemistry journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Khaliullin, F. A.</au><au>Klen, E. E.</au><au>Pavlov, V. N.</au><au>Samorodov, A. V.</au><au>Shepilova, S. O.</au><au>Makarova, N. N.</au><au>Nurlanova, S. N.</au><au>Abzalilov, T. N.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Biological Activity of 5-alkoxy- and 5-amino-substituted 3-bromo-4-nitro-1-(thietan-3-yl)-1H-pyrazoles</atitle><jtitle>Pharmaceutical chemistry journal</jtitle><stitle>Pharm Chem J</stitle><date>2022-06-01</date><risdate>2022</risdate><volume>56</volume><issue>3</issue><spage>316</spage><epage>320</epage><pages>316-320</pages><issn>0091-150X</issn><eissn>1573-9031</eissn><abstract>5-Alkoxy- and 5-amino-substituted 3-bromo-4-nitro-1-(thietan-3-yl)-1
H
-pyrazoles were synthesized by reactions of 3,5-dibromo-4-nitro-1-(thietan-3-yl)-1
H
-pyrazole with sodium alcoholates and primary amines. The structures of the synthesized compounds were established by IR, PMR, and
13
C NMR spectroscopy.
In vitro
studies of the antiplatelet, anticoagulant, and antioxidant activity revealed promising compounds, including 3-bromo-5-methoxy-4-nitro-1-(thietan-3-yl)-1
H
-pyrazole with antioxidant action and 2-{[3-bromo-4-nitro-1-(thietan-3-yl)-1
H
-pyrazol-5-yl]amino}ethan-1-ol with an antiplatelet effect. Results of
in silico
calculations predicted the absence of toxic risks (mutagenicity, oncogenicity, reproductive toxicity, local irritation) and acceptable bioavailability (in terms of the topological polar surface area).</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s11094-022-02636-9</doi><tpages>5</tpages></addata></record> |
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| subjects | Anticoagulants (Medicine) Antioxidants Medicine Nuclear magnetic resonance spectroscopy Organic Chemistry Pharmacology/Toxicology Pharmacy |
| title | Synthesis and Biological Activity of 5-alkoxy- and 5-amino-substituted 3-bromo-4-nitro-1-(thietan-3-yl)-1H-pyrazoles |
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