Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents
New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their structures were identified by different spectroscopic data (1H NMR, 13C NMR, two‐dimensional NMR, mass spectrometry, elemental analysis, and single‐crystal X‐ray analysis). The mechanism describing the formation of t...
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| Veröffentlicht in: | Archiv der Pharmazie (Weinheim) 2021-05, Vol.354 (5), p.e2000336-n/a |
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| creator | Aly, Ashraf A. Hassan, Alaa A. Makhlouf, Maysa M. Alshammari, Mohammed B. Mohamed Naguib Abdel Hafez, Sara Refaie, Marwa M. M. Bräse, Stefan Nieger, Martin Ramadan, Mohamed |
| description | New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their structures were identified by different spectroscopic data (1H NMR, 13C NMR, two‐dimensional NMR, mass spectrometry, elemental analysis, and single‐crystal X‐ray analysis). The mechanism describing the formation of the products was also discussed. The antidiabetic activity of the isolated products was investigated histochemically. The synthesized sulfonylalkylthiosemicarbazide exhibited antihyperglycemic activity in streptozotocin‐induced diabetic mice. Compounds 5a and 5c significantly lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. Also, they caused a significant decrease in malondialdehyde levels and normalized the glutathione levels in streptozotocin‐induced diabetic mice, compared with the diabetic group. The results suggest that the synthesized hydrazinocarbothioamides may effectively inhibit the development of oxidative stress in diabetes.
New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their antidiabetic activity was investigated histochemically after the treatment of streptozotocin‐induced diabetic mice. Compounds 5a and 5c lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. They decreased the malondialdehyde levels and normalized the glutathione levels, thus inhibiting the development of oxidative stress. |
| doi_str_mv | 10.1002/ardp.202000336 |
| format | Article |
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New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their antidiabetic activity was investigated histochemically after the treatment of streptozotocin‐induced diabetic mice. Compounds 5a and 5c lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. They decreased the malondialdehyde levels and normalized the glutathione levels, thus inhibiting the development of oxidative stress.</description><identifier>ISSN: 0365-6233</identifier><identifier>EISSN: 1521-4184</identifier><identifier>DOI: 10.1002/ardp.202000336</identifier><identifier>PMID: 33410162</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>4‐substituted hydrazinecarbothioamides ; Antidiabetics ; antihyperglycemic activity ; bis(2‐(phenylsulfonyl)‐ethyl)sulfane ; Diabetes ; glutathione ; malondialdehyde ; sulfonylalkylthiosemicarbazide</subject><ispartof>Archiv der Pharmazie (Weinheim), 2021-05, Vol.354 (5), p.e2000336-n/a</ispartof><rights>2021 Deutsche Pharmazeutische Gesellschaft</rights><rights>2021 Deutsche Pharmazeutische Gesellschaft.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3736-cee8c0805698b2e8e8d3d6703ac5cd142239c02927314f0f95f964b56ba296dc3</citedby><cites>FETCH-LOGICAL-c3736-cee8c0805698b2e8e8d3d6703ac5cd142239c02927314f0f95f964b56ba296dc3</cites><orcidid>0000-0001-6211-9558 ; 0000-0002-7975-3421 ; 0000-0003-4845-3191 ; 0000-0002-0314-3408</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fardp.202000336$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fardp.202000336$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33410162$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Aly, Ashraf A.</creatorcontrib><creatorcontrib>Hassan, Alaa A.</creatorcontrib><creatorcontrib>Makhlouf, Maysa M.</creatorcontrib><creatorcontrib>Alshammari, Mohammed B.</creatorcontrib><creatorcontrib>Mohamed Naguib Abdel Hafez, Sara</creatorcontrib><creatorcontrib>Refaie, Marwa M. M.</creatorcontrib><creatorcontrib>Bräse, Stefan</creatorcontrib><creatorcontrib>Nieger, Martin</creatorcontrib><creatorcontrib>Ramadan, Mohamed</creatorcontrib><title>Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents</title><title>Archiv der Pharmazie (Weinheim)</title><addtitle>Arch Pharm (Weinheim)</addtitle><description>New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their structures were identified by different spectroscopic data (1H NMR, 13C NMR, two‐dimensional NMR, mass spectrometry, elemental analysis, and single‐crystal X‐ray analysis). The mechanism describing the formation of the products was also discussed. The antidiabetic activity of the isolated products was investigated histochemically. The synthesized sulfonylalkylthiosemicarbazide exhibited antihyperglycemic activity in streptozotocin‐induced diabetic mice. Compounds 5a and 5c significantly lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. Also, they caused a significant decrease in malondialdehyde levels and normalized the glutathione levels in streptozotocin‐induced diabetic mice, compared with the diabetic group. The results suggest that the synthesized hydrazinocarbothioamides may effectively inhibit the development of oxidative stress in diabetes.
New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their antidiabetic activity was investigated histochemically after the treatment of streptozotocin‐induced diabetic mice. Compounds 5a and 5c lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. They decreased the malondialdehyde levels and normalized the glutathione levels, thus inhibiting the development of oxidative stress.</description><subject>4‐substituted hydrazinecarbothioamides</subject><subject>Antidiabetics</subject><subject>antihyperglycemic activity</subject><subject>bis(2‐(phenylsulfonyl)‐ethyl)sulfane</subject><subject>Diabetes</subject><subject>glutathione</subject><subject>malondialdehyde</subject><subject>sulfonylalkylthiosemicarbazide</subject><issn>0365-6233</issn><issn>1521-4184</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkEtLxDAURoMoOo5uXUrBjZuOeTSZdimOLxAU0a0hTW5nIm1Tkxapv94M4wPcuLpc7vk-LgehI4JnBGN6przpZhRTjDFjYgtNCKckzUiebaMJZoKngjK2h_ZDeF0zmPJdtMdYRjARdIJeFhDssk1Ua5Iwtv0qriFxVbIajVcftgWtfOn6lXWqsQaSMNSVayEkKiSd66HtrapjvLersQO_rEcNjdWJWsZTOEA7laoDHH7NKXq-uny6uEnv7q9vL87vUs3mTKQaINc4x1wUeUkhh9wwI-aYKc21IRmlrNCYFnTOSFbhquBVIbKSi1LRQhjNpuh009t59zZA6GVjg4a6Vi24IUiazQWhgpA8oid_0Fc3-DZ-J2l0xwjnUdkUzTaU9i4ED5XsvG2UHyXBcm1ers3LH_MxcPxVO5QNmB_8W3UEig3wbmsY_6mT54-Lh9_yT1kSkEk</recordid><startdate>202105</startdate><enddate>202105</enddate><creator>Aly, Ashraf A.</creator><creator>Hassan, Alaa A.</creator><creator>Makhlouf, Maysa M.</creator><creator>Alshammari, Mohammed B.</creator><creator>Mohamed Naguib Abdel Hafez, Sara</creator><creator>Refaie, Marwa M. M.</creator><creator>Bräse, Stefan</creator><creator>Nieger, Martin</creator><creator>Ramadan, Mohamed</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6211-9558</orcidid><orcidid>https://orcid.org/0000-0002-7975-3421</orcidid><orcidid>https://orcid.org/0000-0003-4845-3191</orcidid><orcidid>https://orcid.org/0000-0002-0314-3408</orcidid></search><sort><creationdate>202105</creationdate><title>Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents</title><author>Aly, Ashraf A. ; Hassan, Alaa A. ; Makhlouf, Maysa M. ; Alshammari, Mohammed B. ; Mohamed Naguib Abdel Hafez, Sara ; Refaie, Marwa M. M. ; Bräse, Stefan ; Nieger, Martin ; Ramadan, Mohamed</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3736-cee8c0805698b2e8e8d3d6703ac5cd142239c02927314f0f95f964b56ba296dc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>4‐substituted hydrazinecarbothioamides</topic><topic>Antidiabetics</topic><topic>antihyperglycemic activity</topic><topic>bis(2‐(phenylsulfonyl)‐ethyl)sulfane</topic><topic>Diabetes</topic><topic>glutathione</topic><topic>malondialdehyde</topic><topic>sulfonylalkylthiosemicarbazide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Aly, Ashraf A.</creatorcontrib><creatorcontrib>Hassan, Alaa A.</creatorcontrib><creatorcontrib>Makhlouf, Maysa M.</creatorcontrib><creatorcontrib>Alshammari, Mohammed B.</creatorcontrib><creatorcontrib>Mohamed Naguib Abdel Hafez, Sara</creatorcontrib><creatorcontrib>Refaie, Marwa M. M.</creatorcontrib><creatorcontrib>Bräse, Stefan</creatorcontrib><creatorcontrib>Nieger, Martin</creatorcontrib><creatorcontrib>Ramadan, Mohamed</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Archiv der Pharmazie (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Aly, Ashraf A.</au><au>Hassan, Alaa A.</au><au>Makhlouf, Maysa M.</au><au>Alshammari, Mohammed B.</au><au>Mohamed Naguib Abdel Hafez, Sara</au><au>Refaie, Marwa M. M.</au><au>Bräse, Stefan</au><au>Nieger, Martin</au><au>Ramadan, Mohamed</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents</atitle><jtitle>Archiv der Pharmazie (Weinheim)</jtitle><addtitle>Arch Pharm (Weinheim)</addtitle><date>2021-05</date><risdate>2021</risdate><volume>354</volume><issue>5</issue><spage>e2000336</spage><epage>n/a</epage><pages>e2000336-n/a</pages><issn>0365-6233</issn><eissn>1521-4184</eissn><abstract>New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their structures were identified by different spectroscopic data (1H NMR, 13C NMR, two‐dimensional NMR, mass spectrometry, elemental analysis, and single‐crystal X‐ray analysis). The mechanism describing the formation of the products was also discussed. The antidiabetic activity of the isolated products was investigated histochemically. The synthesized sulfonylalkylthiosemicarbazide exhibited antihyperglycemic activity in streptozotocin‐induced diabetic mice. Compounds 5a and 5c significantly lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. Also, they caused a significant decrease in malondialdehyde levels and normalized the glutathione levels in streptozotocin‐induced diabetic mice, compared with the diabetic group. The results suggest that the synthesized hydrazinocarbothioamides may effectively inhibit the development of oxidative stress in diabetes.
New hydrazinecarbothioamides with a phenylsulfonyl group were synthesized and their antidiabetic activity was investigated histochemically after the treatment of streptozotocin‐induced diabetic mice. Compounds 5a and 5c lowered the blood glucose level to 103.3 ± 1.8 and 102 ± 3.9 mg/dl, respectively. They decreased the malondialdehyde levels and normalized the glutathione levels, thus inhibiting the development of oxidative stress.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>33410162</pmid><doi>10.1002/ardp.202000336</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0001-6211-9558</orcidid><orcidid>https://orcid.org/0000-0002-7975-3421</orcidid><orcidid>https://orcid.org/0000-0003-4845-3191</orcidid><orcidid>https://orcid.org/0000-0002-0314-3408</orcidid></addata></record> |
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| subjects | 4‐substituted hydrazinecarbothioamides Antidiabetics antihyperglycemic activity bis(2‐(phenylsulfonyl)‐ethyl)sulfane Diabetes glutathione malondialdehyde sulfonylalkylthiosemicarbazide |
| title | Design and synthesis of hydrazinecarbothioamide sulfones as potential antihyperglycemic agents |
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