Loading…
New maleimide 1,2,3-triazole hybrids: design, synthesis, anticancer, and antimicrobial activities
A new series of maleimide triazole hybrid compounds namely 3-chloro-1-[(1-aryl-1 H -1,2,3-triazol-4-yl)methyl]-4-(arylamino)-1 H -pyrrole-2,5-dione have been prepared. Our synthetic strategy starts via the reaction of 2,3-dichloromaleic anhydride with propargyl amine followed by chlorine displacemen...
Saved in:
| Published in: | Monatshefte für Chemie 2020-10, Vol.151 (10), p.1609-1619 |
|---|---|
| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| 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-c356t-4db32f901b0af32c4a8e0922ff7d990109e4b24d39b9036e5cf4cb52b54ee62f3 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c356t-4db32f901b0af32c4a8e0922ff7d990109e4b24d39b9036e5cf4cb52b54ee62f3 |
| container_end_page | 1619 |
| container_issue | 10 |
| container_start_page | 1609 |
| container_title | Monatshefte für Chemie |
| container_volume | 151 |
| creator | Salameh, Bader A. Abu-Safieh, Kayed A. Al-Hushki, Eman H. Talib, Wamidh H. Al-ataby, Israa A. Al-Qawasmeh, Raed A. |
| description | A new series of maleimide triazole hybrid compounds namely 3-chloro-1-[(1-aryl-1
H
-1,2,3-triazol-4-yl)methyl]-4-(arylamino)-1
H
-pyrrole-2,5-dione have been prepared. Our synthetic strategy starts via the reaction of 2,3-dichloromaleic anhydride with propargyl amine followed by chlorine displacement with arylamine and subsequent formation of a triazole utilizing copper(I) catalyzed azide-alkyne cycloaddition reaction, that generates the designed triazole nucleus. The produced hybrid compounds were identified using various physicochemical properties of the pure compounds. The synthesized compounds were screened for antimicrobial activities against
Escherichia coli
,
Pseudomonas aeruginosa,
and
Bacillus spizizenii
. While selected compounds were tested for their anticancer activities against T47D, HCT 116, and VERO cell lines.
Graphic abstract |
| doi_str_mv | 10.1007/s00706-020-02685-4 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2473814519</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2473814519</sourcerecordid><originalsourceid>FETCH-LOGICAL-c356t-4db32f901b0af32c4a8e0922ff7d990109e4b24d39b9036e5cf4cb52b54ee62f3</originalsourceid><addsrcrecordid>eNp9UMlOwzAUtBBIlMIPcIrENQZvSWpuqGKTKrjA2bKd59ZVlmKnoPL1uA0SNw5v1cxbBqFLSq4pIdVNTI6UmDCSrJwVWByhCRVcYCGq4hhNSGpjyUR1is5iXJNUC8InSL_AV9bqBnzra8hoznKOh-D1d99AttqZ4Ot4m9UQ_bLLs7jrhlXKY57pbvBWdxbCPq8Pdett6I3XTabt4D_94CGeoxOnmwgXv3GK3h_u3-ZPePH6-Dy_W2DLi3LAojacOUmoIdpxZoWeAZGMOVfVMrWJBGGYqLk0kvASCuuENQUzhQAomeNTdDXO3YT-YwtxUOt-G7q0UqW3-YyKgsqEYiMqHRpjAKc2wbc67BQlai-lGqVUSUp1kFKJROIjKSZwt4TwN_of1g8V13Z8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2473814519</pqid></control><display><type>article</type><title>New maleimide 1,2,3-triazole hybrids: design, synthesis, anticancer, and antimicrobial activities</title><source>Springer Link</source><creator>Salameh, Bader A. ; Abu-Safieh, Kayed A. ; Al-Hushki, Eman H. ; Talib, Wamidh H. ; Al-ataby, Israa A. ; Al-Qawasmeh, Raed A.</creator><creatorcontrib>Salameh, Bader A. ; Abu-Safieh, Kayed A. ; Al-Hushki, Eman H. ; Talib, Wamidh H. ; Al-ataby, Israa A. ; Al-Qawasmeh, Raed A.</creatorcontrib><description>A new series of maleimide triazole hybrid compounds namely 3-chloro-1-[(1-aryl-1
H
-1,2,3-triazol-4-yl)methyl]-4-(arylamino)-1
H
-pyrrole-2,5-dione have been prepared. Our synthetic strategy starts via the reaction of 2,3-dichloromaleic anhydride with propargyl amine followed by chlorine displacement with arylamine and subsequent formation of a triazole utilizing copper(I) catalyzed azide-alkyne cycloaddition reaction, that generates the designed triazole nucleus. The produced hybrid compounds were identified using various physicochemical properties of the pure compounds. The synthesized compounds were screened for antimicrobial activities against
Escherichia coli
,
Pseudomonas aeruginosa,
and
Bacillus spizizenii
. While selected compounds were tested for their anticancer activities against T47D, HCT 116, and VERO cell lines.
Graphic abstract</description><identifier>ISSN: 0026-9247</identifier><identifier>EISSN: 1434-4475</identifier><identifier>DOI: 10.1007/s00706-020-02685-4</identifier><language>eng</language><publisher>Vienna: Springer Vienna</publisher><subject>Alkynes ; Amines ; Analytical Chemistry ; Anticancer properties ; Antiinfectives and antibacterials ; Aromatic compounds ; Cancer ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Chlorine ; Cycloaddition ; Diketones ; E coli ; Inorganic Chemistry ; Organic Chemistry ; Organic compounds ; Original Paper ; Physical Chemistry ; Pseudomonas aeruginosa ; Theoretical and Computational Chemistry ; Triazoles</subject><ispartof>Monatshefte für Chemie, 2020-10, Vol.151 (10), p.1609-1619</ispartof><rights>Springer-Verlag GmbH Austria, part of Springer Nature 2020</rights><rights>Springer-Verlag GmbH Austria, part of Springer Nature 2020.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-4db32f901b0af32c4a8e0922ff7d990109e4b24d39b9036e5cf4cb52b54ee62f3</citedby><cites>FETCH-LOGICAL-c356t-4db32f901b0af32c4a8e0922ff7d990109e4b24d39b9036e5cf4cb52b54ee62f3</cites><orcidid>0000-0003-2041-2486</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>Salameh, Bader A.</creatorcontrib><creatorcontrib>Abu-Safieh, Kayed A.</creatorcontrib><creatorcontrib>Al-Hushki, Eman H.</creatorcontrib><creatorcontrib>Talib, Wamidh H.</creatorcontrib><creatorcontrib>Al-ataby, Israa A.</creatorcontrib><creatorcontrib>Al-Qawasmeh, Raed A.</creatorcontrib><title>New maleimide 1,2,3-triazole hybrids: design, synthesis, anticancer, and antimicrobial activities</title><title>Monatshefte für Chemie</title><addtitle>Monatsh Chem</addtitle><description>A new series of maleimide triazole hybrid compounds namely 3-chloro-1-[(1-aryl-1
H
-1,2,3-triazol-4-yl)methyl]-4-(arylamino)-1
H
-pyrrole-2,5-dione have been prepared. Our synthetic strategy starts via the reaction of 2,3-dichloromaleic anhydride with propargyl amine followed by chlorine displacement with arylamine and subsequent formation of a triazole utilizing copper(I) catalyzed azide-alkyne cycloaddition reaction, that generates the designed triazole nucleus. The produced hybrid compounds were identified using various physicochemical properties of the pure compounds. The synthesized compounds were screened for antimicrobial activities against
Escherichia coli
,
Pseudomonas aeruginosa,
and
Bacillus spizizenii
. While selected compounds were tested for their anticancer activities against T47D, HCT 116, and VERO cell lines.
Graphic abstract</description><subject>Alkynes</subject><subject>Amines</subject><subject>Analytical Chemistry</subject><subject>Anticancer properties</subject><subject>Antiinfectives and antibacterials</subject><subject>Aromatic compounds</subject><subject>Cancer</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Chlorine</subject><subject>Cycloaddition</subject><subject>Diketones</subject><subject>E coli</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><subject>Organic compounds</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Pseudomonas aeruginosa</subject><subject>Theoretical and Computational Chemistry</subject><subject>Triazoles</subject><issn>0026-9247</issn><issn>1434-4475</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9UMlOwzAUtBBIlMIPcIrENQZvSWpuqGKTKrjA2bKd59ZVlmKnoPL1uA0SNw5v1cxbBqFLSq4pIdVNTI6UmDCSrJwVWByhCRVcYCGq4hhNSGpjyUR1is5iXJNUC8InSL_AV9bqBnzra8hoznKOh-D1d99AttqZ4Ot4m9UQ_bLLs7jrhlXKY57pbvBWdxbCPq8Pdett6I3XTabt4D_94CGeoxOnmwgXv3GK3h_u3-ZPePH6-Dy_W2DLi3LAojacOUmoIdpxZoWeAZGMOVfVMrWJBGGYqLk0kvASCuuENQUzhQAomeNTdDXO3YT-YwtxUOt-G7q0UqW3-YyKgsqEYiMqHRpjAKc2wbc67BQlai-lGqVUSUp1kFKJROIjKSZwt4TwN_of1g8V13Z8</recordid><startdate>20201001</startdate><enddate>20201001</enddate><creator>Salameh, Bader A.</creator><creator>Abu-Safieh, Kayed A.</creator><creator>Al-Hushki, Eman H.</creator><creator>Talib, Wamidh H.</creator><creator>Al-ataby, Israa A.</creator><creator>Al-Qawasmeh, Raed A.</creator><general>Springer Vienna</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-2041-2486</orcidid></search><sort><creationdate>20201001</creationdate><title>New maleimide 1,2,3-triazole hybrids: design, synthesis, anticancer, and antimicrobial activities</title><author>Salameh, Bader A. ; Abu-Safieh, Kayed A. ; Al-Hushki, Eman H. ; Talib, Wamidh H. ; Al-ataby, Israa A. ; Al-Qawasmeh, Raed A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-4db32f901b0af32c4a8e0922ff7d990109e4b24d39b9036e5cf4cb52b54ee62f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkynes</topic><topic>Amines</topic><topic>Analytical Chemistry</topic><topic>Anticancer properties</topic><topic>Antiinfectives and antibacterials</topic><topic>Aromatic compounds</topic><topic>Cancer</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Chlorine</topic><topic>Cycloaddition</topic><topic>Diketones</topic><topic>E coli</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Organic compounds</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Pseudomonas aeruginosa</topic><topic>Theoretical and Computational Chemistry</topic><topic>Triazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Salameh, Bader A.</creatorcontrib><creatorcontrib>Abu-Safieh, Kayed A.</creatorcontrib><creatorcontrib>Al-Hushki, Eman H.</creatorcontrib><creatorcontrib>Talib, Wamidh H.</creatorcontrib><creatorcontrib>Al-ataby, Israa A.</creatorcontrib><creatorcontrib>Al-Qawasmeh, Raed A.</creatorcontrib><collection>CrossRef</collection><jtitle>Monatshefte für Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Salameh, Bader A.</au><au>Abu-Safieh, Kayed A.</au><au>Al-Hushki, Eman H.</au><au>Talib, Wamidh H.</au><au>Al-ataby, Israa A.</au><au>Al-Qawasmeh, Raed A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New maleimide 1,2,3-triazole hybrids: design, synthesis, anticancer, and antimicrobial activities</atitle><jtitle>Monatshefte für Chemie</jtitle><stitle>Monatsh Chem</stitle><date>2020-10-01</date><risdate>2020</risdate><volume>151</volume><issue>10</issue><spage>1609</spage><epage>1619</epage><pages>1609-1619</pages><issn>0026-9247</issn><eissn>1434-4475</eissn><abstract>A new series of maleimide triazole hybrid compounds namely 3-chloro-1-[(1-aryl-1
H
-1,2,3-triazol-4-yl)methyl]-4-(arylamino)-1
H
-pyrrole-2,5-dione have been prepared. Our synthetic strategy starts via the reaction of 2,3-dichloromaleic anhydride with propargyl amine followed by chlorine displacement with arylamine and subsequent formation of a triazole utilizing copper(I) catalyzed azide-alkyne cycloaddition reaction, that generates the designed triazole nucleus. The produced hybrid compounds were identified using various physicochemical properties of the pure compounds. The synthesized compounds were screened for antimicrobial activities against
Escherichia coli
,
Pseudomonas aeruginosa,
and
Bacillus spizizenii
. While selected compounds were tested for their anticancer activities against T47D, HCT 116, and VERO cell lines.
Graphic abstract</abstract><cop>Vienna</cop><pub>Springer Vienna</pub><doi>10.1007/s00706-020-02685-4</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0003-2041-2486</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0026-9247 |
| ispartof | Monatshefte für Chemie, 2020-10, Vol.151 (10), p.1609-1619 |
| issn | 0026-9247 1434-4475 |
| language | eng |
| recordid | cdi_proquest_journals_2473814519 |
| source | Springer Link |
| subjects | Alkynes Amines Analytical Chemistry Anticancer properties Antiinfectives and antibacterials Aromatic compounds Cancer Chemistry Chemistry and Materials Science Chemistry/Food Science Chlorine Cycloaddition Diketones E coli Inorganic Chemistry Organic Chemistry Organic compounds Original Paper Physical Chemistry Pseudomonas aeruginosa Theoretical and Computational Chemistry Triazoles |
| title | New maleimide 1,2,3-triazole hybrids: design, synthesis, anticancer, and antimicrobial activities |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-01T10%3A32%3A42IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=New%20maleimide%201,2,3-triazole%20hybrids:%20design,%20synthesis,%20anticancer,%20and%20antimicrobial%20activities&rft.jtitle=Monatshefte%20f%C3%BCr%20Chemie&rft.au=Salameh,%20Bader%20A.&rft.date=2020-10-01&rft.volume=151&rft.issue=10&rft.spage=1609&rft.epage=1619&rft.pages=1609-1619&rft.issn=0026-9247&rft.eissn=1434-4475&rft_id=info:doi/10.1007/s00706-020-02685-4&rft_dat=%3Cproquest_cross%3E2473814519%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c356t-4db32f901b0af32c4a8e0922ff7d990109e4b24d39b9036e5cf4cb52b54ee62f3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2473814519&rft_id=info:pmid/&rfr_iscdi=true |