Molecular Orbital Studies of Antischistosomal Agents
Molecular orbital calculations were used to investigate the antischistosomal agent, niridazole, and an inactive derivative, 1‐(5‐nitro‐2‐thiazolyl)‐2‐ethylurea. The CNDO/2 calculations revealed that the inactive derivative had a preferred conformation stabilized by an intramolecular hydrogen bond. T...
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| Veröffentlicht in: | Journal of pharmaceutical sciences 1976-11, Vol.65 (11), p.1704-1705 |
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| container_end_page | 1705 |
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| container_issue | 11 |
| container_start_page | 1704 |
| container_title | Journal of pharmaceutical sciences |
| container_volume | 65 |
| creator | Aldrich, Haven S. Clagett, Donald C. |
| description | Molecular orbital calculations were used to investigate the antischistosomal agent, niridazole, and an inactive derivative, 1‐(5‐nitro‐2‐thiazolyl)‐2‐ethylurea. The CNDO/2 calculations revealed that the inactive derivative had a preferred conformation stabilized by an intramolecular hydrogen bond. The molecular profile, the relative three‐dimensional arrangement of constituent atoms, of the inactive derivative was different than that of the niridazole compound. The likelihood of similar intramolecular interactions rendering niridazole derivatives inactive is discussed. The results of the calculations suggest select structural modifications that might increase the efficacy of niridazole derivatives. |
| doi_str_mv | 10.1002/jps.2600651138 |
| format | Article |
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The CNDO/2 calculations revealed that the inactive derivative had a preferred conformation stabilized by an intramolecular hydrogen bond. The molecular profile, the relative three‐dimensional arrangement of constituent atoms, of the inactive derivative was different than that of the niridazole compound. The likelihood of similar intramolecular interactions rendering niridazole derivatives inactive is discussed. The results of the calculations suggest select structural modifications that might increase the efficacy of niridazole derivatives.</description><identifier>ISSN: 0022-3549</identifier><identifier>EISSN: 1520-6017</identifier><identifier>DOI: 10.1002/jps.2600651138</identifier><identifier>PMID: 994009</identifier><language>eng</language><publisher>Washington: Elsevier Inc</publisher><subject>Antischistosomal agents-niridazole ; Antischistosomal agents—niridazole, preferred molecular conformation, effect on biological activity ; Chemical Phenomena ; Chemistry ; effect on biological activity ; Molecular Conformation ; Molecular orbital calculations-preferred conformations of niridazole and derivative ; Niridazole - analogs & derivatives ; Niridazole and derivative-preferred molecular conformations ; Niridazole and derivative—preferred molecular conformations, effect on biological activity ; preferred molecular conformation ; preferred molecular conformations ; Quantum Theory ; Schistosomicides ; Structure-Activity Relationship ; Structure-activity relationships-niridazole and derivative ; Structure‐activity relationships—niridazole and derivative, preferred molecular conformations, effect on biological activity</subject><ispartof>Journal of pharmaceutical sciences, 1976-11, Vol.65 (11), p.1704-1705</ispartof><rights>1976 Wiley‐Liss, Inc., A Wiley Company</rights><rights>Copyright © 1976 Wiley‐Liss, Inc., A Wiley Company</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjps.2600651138$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjps.2600651138$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/994009$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Aldrich, Haven S.</creatorcontrib><creatorcontrib>Clagett, Donald C.</creatorcontrib><title>Molecular Orbital Studies of Antischistosomal Agents</title><title>Journal of pharmaceutical sciences</title><addtitle>J. Pharm. Sci</addtitle><description>Molecular orbital calculations were used to investigate the antischistosomal agent, niridazole, and an inactive derivative, 1‐(5‐nitro‐2‐thiazolyl)‐2‐ethylurea. The CNDO/2 calculations revealed that the inactive derivative had a preferred conformation stabilized by an intramolecular hydrogen bond. The molecular profile, the relative three‐dimensional arrangement of constituent atoms, of the inactive derivative was different than that of the niridazole compound. The likelihood of similar intramolecular interactions rendering niridazole derivatives inactive is discussed. The results of the calculations suggest select structural modifications that might increase the efficacy of niridazole derivatives.</description><subject>Antischistosomal agents-niridazole</subject><subject>Antischistosomal agents—niridazole, preferred molecular conformation, effect on biological activity</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>effect on biological activity</subject><subject>Molecular Conformation</subject><subject>Molecular orbital calculations-preferred conformations of niridazole and derivative</subject><subject>Niridazole - analogs & derivatives</subject><subject>Niridazole and derivative-preferred molecular conformations</subject><subject>Niridazole and derivative—preferred molecular conformations, effect on biological activity</subject><subject>preferred molecular conformation</subject><subject>preferred molecular conformations</subject><subject>Quantum Theory</subject><subject>Schistosomicides</subject><subject>Structure-Activity Relationship</subject><subject>Structure-activity relationships-niridazole and derivative</subject><subject>Structure‐activity relationships—niridazole and derivative, preferred molecular conformations, effect on biological activity</subject><issn>0022-3549</issn><issn>1520-6017</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1976</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkLlPwzAchS3EVQorE0MnthRfceyxIE6VQ4CExGIlzi9gyFHsBOh_j6tUIAaEPHh433uyP4R2CR4TjOnBy8yPqcBYxIQwuYIGJKY4Epgkq2gQABqxmKtNtOX9Cw4YjuMNtK4Ux1gNEL9sSjBdmbrRtctsm5aju7bLLfhRU4wmdWu9eba-bXxThWzyBHXrt9FakZYedpb3EN2fHN8fnUXT69Pzo8k0MkwSGSWUG6myhErCi1xwwwyXBcsFYSIFzk3KRaYIJAUvEkyNNFQRtjjKZBTYEO33szPXvHXgW12F10BZpjU0ndeSCSwFkQEc96BxjfcOCj1ztkrdXBOsF5J0kKR_JIXC3nK5yyrIv_HeSohVH3_YEub_jOmLm7tf01HfDdLg87ubulctEpbE-uHqVMfTQ34l6a1-DLzseQgi3y047Y2F2kBuHZhW54396xdfCQyTfA</recordid><startdate>197611</startdate><enddate>197611</enddate><creator>Aldrich, Haven S.</creator><creator>Clagett, Donald C.</creator><general>Elsevier Inc</general><general>Wiley Subscription Services, Inc., A Wiley Company</general><scope>BSCLL</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>197611</creationdate><title>Molecular Orbital Studies of Antischistosomal Agents</title><author>Aldrich, Haven S. ; Clagett, Donald C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3818-724c89b72814fd64c3c48f3d6136ae44ca46b91e7f4f702c8c291313139cb2e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1976</creationdate><topic>Antischistosomal agents-niridazole</topic><topic>Antischistosomal agents—niridazole, preferred molecular conformation, effect on biological activity</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>effect on biological activity</topic><topic>Molecular Conformation</topic><topic>Molecular orbital calculations-preferred conformations of niridazole and derivative</topic><topic>Niridazole - analogs & derivatives</topic><topic>Niridazole and derivative-preferred molecular conformations</topic><topic>Niridazole and derivative—preferred molecular conformations, effect on biological activity</topic><topic>preferred molecular conformation</topic><topic>preferred molecular conformations</topic><topic>Quantum Theory</topic><topic>Schistosomicides</topic><topic>Structure-Activity Relationship</topic><topic>Structure-activity relationships-niridazole and derivative</topic><topic>Structure‐activity relationships—niridazole and derivative, preferred molecular conformations, effect on biological activity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Aldrich, Haven S.</creatorcontrib><creatorcontrib>Clagett, Donald C.</creatorcontrib><collection>Istex</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>Journal of pharmaceutical sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Aldrich, Haven S.</au><au>Clagett, Donald C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Molecular Orbital Studies of Antischistosomal Agents</atitle><jtitle>Journal of pharmaceutical sciences</jtitle><addtitle>J. Pharm. Sci</addtitle><date>1976-11</date><risdate>1976</risdate><volume>65</volume><issue>11</issue><spage>1704</spage><epage>1705</epage><pages>1704-1705</pages><issn>0022-3549</issn><eissn>1520-6017</eissn><abstract>Molecular orbital calculations were used to investigate the antischistosomal agent, niridazole, and an inactive derivative, 1‐(5‐nitro‐2‐thiazolyl)‐2‐ethylurea. The CNDO/2 calculations revealed that the inactive derivative had a preferred conformation stabilized by an intramolecular hydrogen bond. The molecular profile, the relative three‐dimensional arrangement of constituent atoms, of the inactive derivative was different than that of the niridazole compound. The likelihood of similar intramolecular interactions rendering niridazole derivatives inactive is discussed. The results of the calculations suggest select structural modifications that might increase the efficacy of niridazole derivatives.</abstract><cop>Washington</cop><pub>Elsevier Inc</pub><pmid>994009</pmid><doi>10.1002/jps.2600651138</doi><tpages>2</tpages></addata></record> |
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| ispartof | Journal of pharmaceutical sciences, 1976-11, Vol.65 (11), p.1704-1705 |
| issn | 0022-3549 1520-6017 |
| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete; Alma/SFX Local Collection |
| subjects | Antischistosomal agents-niridazole Antischistosomal agents—niridazole, preferred molecular conformation, effect on biological activity Chemical Phenomena Chemistry effect on biological activity Molecular Conformation Molecular orbital calculations-preferred conformations of niridazole and derivative Niridazole - analogs & derivatives Niridazole and derivative-preferred molecular conformations Niridazole and derivative—preferred molecular conformations, effect on biological activity preferred molecular conformation preferred molecular conformations Quantum Theory Schistosomicides Structure-Activity Relationship Structure-activity relationships-niridazole and derivative Structure‐activity relationships—niridazole and derivative, preferred molecular conformations, effect on biological activity |
| title | Molecular Orbital Studies of Antischistosomal Agents |
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