Stieglitz rearrangement of N, N-dichloro-β,β-disubstituted taurines under mild aqueous conditions
The structure–stability relationship (SSR) of alkyl and cycloalkyl β-substitutions on N, N-dichlorotaurines reveals order-of-magnitude changes in their aqueous (pH 4–7, 20–40 °C) stabilities. Stieglitz rearrangement is one of the mechanisms of decomposition and produces β-ketosulfonic acids and chlo...
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creator | Shiau, Timothy P. Houchin, Ashley Nair, Satheesh Xu, Ping Low, Eddy Najafi, Ramin (Ron) Jain, Rakesh |
description | The structure–stability relationship (SSR) of alkyl and cycloalkyl β-substitutions on
N,
N-dichlorotaurines reveals order-of-magnitude changes in their aqueous (pH 4–7, 20–40
°C) stabilities. Stieglitz rearrangement is one of the mechanisms of decomposition and produces β-ketosulfonic acids and chlorinated derivatives thereof.
New topical anti-infectives comprised of
N,
N-dichloro-β,β-disubstituted taurines [
Tetrahedron Lett.
2008,
49, 2193;
Biorg. Med. Chem. Lett.
2009,
19, 196] have been examined for structure–stability relationships (SSR) based upon various alkyl, heteroalkyl and cycloalkyl β-substitutions. These substitutions affect order-of-magnitude changes in the aqueous stability of these
N,
N-dichloroamines which can undergo Stieglitz rearrangement of alkyl groups under extremely mild conditions (H
2O, pH 4–7, 0–20
mM acetate or phosphate buffer, 20–40
°C). This process produces β-ketosulfonic acids which function as substrates for chlorination by the
N-chlorotaurines which leads to their further degradation. |
doi_str_mv | 10.1016/j.bmcl.2008.12.109 |
format | Article |
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N,
N-dichlorotaurines reveals order-of-magnitude changes in their aqueous (pH 4–7, 20–40
°C) stabilities. Stieglitz rearrangement is one of the mechanisms of decomposition and produces β-ketosulfonic acids and chlorinated derivatives thereof.
New topical anti-infectives comprised of
N,
N-dichloro-β,β-disubstituted taurines [
Tetrahedron Lett.
2008,
49, 2193;
Biorg. Med. Chem. Lett.
2009,
19, 196] have been examined for structure–stability relationships (SSR) based upon various alkyl, heteroalkyl and cycloalkyl β-substitutions. These substitutions affect order-of-magnitude changes in the aqueous stability of these
N,
N-dichloroamines which can undergo Stieglitz rearrangement of alkyl groups under extremely mild conditions (H
2O, pH 4–7, 0–20
mM acetate or phosphate buffer, 20–40
°C). This process produces β-ketosulfonic acids which function as substrates for chlorination by the
N-chlorotaurines which leads to their further degradation.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2008.12.109</identifier><identifier>PMID: 19167221</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antimicrobial ; Chloroamines ; Chlorotaurine ; Combinatorial Chemistry Techniques ; Dichloroamines ; Hydrocarbons, Chlorinated - chemical synthesis ; Hydrocarbons, Chlorinated - chemistry ; Hydrocarbons, Chlorinated - pharmacology ; Molecular Structure ; Rearrangement ; Stereoisomerism ; Stieglitz ; Structure-Activity Relationship ; Sulfinimine addition ; Taurine ; Taurine - analogs & derivatives ; Taurine - chemical synthesis ; Taurine - chemistry ; Taurine - pharmacology ; Water - chemistry</subject><ispartof>Bioorganic & medicinal chemistry letters, 2009-02, Vol.19 (4), p.1110-1114</ispartof><rights>2009 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c385t-9c17ea404b0fb98650709228e93e220cc5f9136d5b0f3ee37a3663550a18a1653</citedby><cites>FETCH-LOGICAL-c385t-9c17ea404b0fb98650709228e93e220cc5f9136d5b0f3ee37a3663550a18a1653</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2008.12.109$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19167221$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shiau, Timothy P.</creatorcontrib><creatorcontrib>Houchin, Ashley</creatorcontrib><creatorcontrib>Nair, Satheesh</creatorcontrib><creatorcontrib>Xu, Ping</creatorcontrib><creatorcontrib>Low, Eddy</creatorcontrib><creatorcontrib>Najafi, Ramin (Ron)</creatorcontrib><creatorcontrib>Jain, Rakesh</creatorcontrib><title>Stieglitz rearrangement of N, N-dichloro-β,β-disubstituted taurines under mild aqueous conditions</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The structure–stability relationship (SSR) of alkyl and cycloalkyl β-substitutions on
N,
N-dichlorotaurines reveals order-of-magnitude changes in their aqueous (pH 4–7, 20–40
°C) stabilities. Stieglitz rearrangement is one of the mechanisms of decomposition and produces β-ketosulfonic acids and chlorinated derivatives thereof.
New topical anti-infectives comprised of
N,
N-dichloro-β,β-disubstituted taurines [
Tetrahedron Lett.
2008,
49, 2193;
Biorg. Med. Chem. Lett.
2009,
19, 196] have been examined for structure–stability relationships (SSR) based upon various alkyl, heteroalkyl and cycloalkyl β-substitutions. These substitutions affect order-of-magnitude changes in the aqueous stability of these
N,
N-dichloroamines which can undergo Stieglitz rearrangement of alkyl groups under extremely mild conditions (H
2O, pH 4–7, 0–20
mM acetate or phosphate buffer, 20–40
°C). This process produces β-ketosulfonic acids which function as substrates for chlorination by the
N-chlorotaurines which leads to their further degradation.</description><subject>Antimicrobial</subject><subject>Chloroamines</subject><subject>Chlorotaurine</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Dichloroamines</subject><subject>Hydrocarbons, Chlorinated - chemical synthesis</subject><subject>Hydrocarbons, Chlorinated - chemistry</subject><subject>Hydrocarbons, Chlorinated - pharmacology</subject><subject>Molecular Structure</subject><subject>Rearrangement</subject><subject>Stereoisomerism</subject><subject>Stieglitz</subject><subject>Structure-Activity Relationship</subject><subject>Sulfinimine addition</subject><subject>Taurine</subject><subject>Taurine - analogs & derivatives</subject><subject>Taurine - chemical synthesis</subject><subject>Taurine - chemistry</subject><subject>Taurine - pharmacology</subject><subject>Water - chemistry</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcFu1DAQhq2Kql1KX6AH5BOnZuuxEyeWuKAKKFJVDoDEzXLsSfEqiYvtVILH6oP0mXC0K3GD02hmvvn1a35CLoBtgYG82m37yY5bzli3BV5m6ohsoJZ1JWrWvCAbpiSrOlV_PyUvU9oxBjWr6xNyCgpkyzlsiP2SPd6PPv-mEU2MZr7HCedMw0DvLuld5bz9MYYYqueny-en0qalT9nnJaOj2SzRz5joMjuMdPKjo-bngmFJ1IbZ-ezDnF6R48GMCc8P9Yx8-_D-6_VNdfv546frd7eVFV2TK2WhRVMc9mzoVScb1jLFeYdKIOfM2mZQIKRryl4gitYIKUXTMAOdAdmIM_Jmr_sQQzGRsp58sjiOZl4daSkVF6JV_wU5Ewo6gALyPWhjSCnioB-in0z8pYHpNQO902sGes1AAy-zVf31QX3pJ3R_Tw5PL8DbPYDlGY8eo07W42zR-Yg2axf8v_T_AA7rmaM</recordid><startdate>20090215</startdate><enddate>20090215</enddate><creator>Shiau, Timothy P.</creator><creator>Houchin, Ashley</creator><creator>Nair, Satheesh</creator><creator>Xu, Ping</creator><creator>Low, Eddy</creator><creator>Najafi, Ramin (Ron)</creator><creator>Jain, Rakesh</creator><general>Elsevier Ltd</general><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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20090215</creationdate><title>Stieglitz rearrangement of N, N-dichloro-β,β-disubstituted taurines under mild aqueous conditions</title><author>Shiau, Timothy P. ; Houchin, Ashley ; Nair, Satheesh ; Xu, Ping ; Low, Eddy ; Najafi, Ramin (Ron) ; Jain, Rakesh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c385t-9c17ea404b0fb98650709228e93e220cc5f9136d5b0f3ee37a3663550a18a1653</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Antimicrobial</topic><topic>Chloroamines</topic><topic>Chlorotaurine</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Dichloroamines</topic><topic>Hydrocarbons, Chlorinated - chemical synthesis</topic><topic>Hydrocarbons, Chlorinated - chemistry</topic><topic>Hydrocarbons, Chlorinated - pharmacology</topic><topic>Molecular Structure</topic><topic>Rearrangement</topic><topic>Stereoisomerism</topic><topic>Stieglitz</topic><topic>Structure-Activity Relationship</topic><topic>Sulfinimine addition</topic><topic>Taurine</topic><topic>Taurine - analogs & derivatives</topic><topic>Taurine - chemical synthesis</topic><topic>Taurine - chemistry</topic><topic>Taurine - pharmacology</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shiau, Timothy P.</creatorcontrib><creatorcontrib>Houchin, Ashley</creatorcontrib><creatorcontrib>Nair, Satheesh</creatorcontrib><creatorcontrib>Xu, Ping</creatorcontrib><creatorcontrib>Low, Eddy</creatorcontrib><creatorcontrib>Najafi, Ramin (Ron)</creatorcontrib><creatorcontrib>Jain, Rakesh</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shiau, Timothy P.</au><au>Houchin, Ashley</au><au>Nair, Satheesh</au><au>Xu, Ping</au><au>Low, Eddy</au><au>Najafi, Ramin (Ron)</au><au>Jain, Rakesh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stieglitz rearrangement of N, N-dichloro-β,β-disubstituted taurines under mild aqueous conditions</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2009-02-15</date><risdate>2009</risdate><volume>19</volume><issue>4</issue><spage>1110</spage><epage>1114</epage><pages>1110-1114</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The structure–stability relationship (SSR) of alkyl and cycloalkyl β-substitutions on
N,
N-dichlorotaurines reveals order-of-magnitude changes in their aqueous (pH 4–7, 20–40
°C) stabilities. Stieglitz rearrangement is one of the mechanisms of decomposition and produces β-ketosulfonic acids and chlorinated derivatives thereof.
New topical anti-infectives comprised of
N,
N-dichloro-β,β-disubstituted taurines [
Tetrahedron Lett.
2008,
49, 2193;
Biorg. Med. Chem. Lett.
2009,
19, 196] have been examined for structure–stability relationships (SSR) based upon various alkyl, heteroalkyl and cycloalkyl β-substitutions. These substitutions affect order-of-magnitude changes in the aqueous stability of these
N,
N-dichloroamines which can undergo Stieglitz rearrangement of alkyl groups under extremely mild conditions (H
2O, pH 4–7, 0–20
mM acetate or phosphate buffer, 20–40
°C). This process produces β-ketosulfonic acids which function as substrates for chlorination by the
N-chlorotaurines which leads to their further degradation.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>19167221</pmid><doi>10.1016/j.bmcl.2008.12.109</doi><tpages>5</tpages></addata></record> |
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subjects | Antimicrobial Chloroamines Chlorotaurine Combinatorial Chemistry Techniques Dichloroamines Hydrocarbons, Chlorinated - chemical synthesis Hydrocarbons, Chlorinated - chemistry Hydrocarbons, Chlorinated - pharmacology Molecular Structure Rearrangement Stereoisomerism Stieglitz Structure-Activity Relationship Sulfinimine addition Taurine Taurine - analogs & derivatives Taurine - chemical synthesis Taurine - chemistry Taurine - pharmacology Water - chemistry |
title | Stieglitz rearrangement of N, N-dichloro-β,β-disubstituted taurines under mild aqueous conditions |
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