4&prime;-(2H-tetrazol-5-yl)-[1,1&prime;-biphenyl]-4-carboxylic acid: Synthetic approaches, single crystal X-ray structures and antimicrobial activity of intermediates

Ardeleanu Rodinel; Dascălu Andrei Ioan; Shova Sergiu; Nicolescu Alina Florica; Roşca Irina; Bratanovici Bogdan Ionel; Lozan Vasile; Roman Gheorghe

Conţinutul numărului revistei

Articolul precedent

Articolul urmator

981

SM ISO690:2012

ARDELEANU, Rodinel, DASCĂLU, Andrei Ioan, SHOVA, Sergiu, NICOLESCU, Alina Florica, ROŞCA, Irina, BRATANOVICI, Bogdan Ionel, LOZAN, Vasile, ROMAN, Gheorghe. 4′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-carboxylic acid: Synthetic approaches, single crystal X-ray structures and antimicrobial activity of intermediates. In: Journal of Molecular Structure, 2018, nr. 1173, pp. 63-71. ISSN 0022-2860. DOI: https://doi.org/10.1016/j.molstruc.2018.06.086

EXPORT metadate:
Google Scholar
Crossref
CERIF

DataCite
Dublin Core

Journal of Molecular Structure

Numărul 1173 / 2018 / ISSN 0022-2860

4′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-carboxylic acid: Synthetic approaches, single crystal X-ray structures and antimicrobial activity of intermediates

DOI:https://doi.org/10.1016/j.molstruc.2018.06.086

Pag. 63-71

Ardeleanu Rodinel¹, Dascălu Andrei Ioan¹, Shova Sergiu¹, Nicolescu Alina Florica¹, Roşca Irina¹, Bratanovici Bogdan Ionel¹², Lozan Vasile¹³, Roman Gheorghe¹

¹ “Petru Poni” Institute of Macromolecular Chemistry,
² Alexandru Ioan Cuza University of Iaşi,
³ Institute of Chemistry of the Academy of Sciences of Moldova

Disponibil în IBN: 7 august 2018

Rezumat

Two synthetic approaches towards 4′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-carboxylic acid, a valuable organic ligand for the preparation of metal-organic frameworks, are reported. The first reaction sequence leading to the target compound comprises the iodination of [1,1′-biphenyl]-4-carboxylic acid, formation of the methyl ester of 4′-iodo-[1,1′-biphenyl]-4-carboxylic acid, nucleophilic substitution of iodine with cyano, ring closure of tetrazole, and hydrolysis of the ester function. The second synthetic pathway starts from 4-bromobenzonitrile, which is converted through Suzuki coupling with 4-carboxyphenylboronic acid into 4′-cyano-[1,1′-biphenyl]-4-carboxylic acid, which in turn leads to the desired compound after ring closure of tetrazole. All of the synthesized compounds have been fully characterized by IR and ¹H- and ¹³C-NMR spectroscopy. Single crystal X-ray structures are reported for the target compound and for methyl esters of 4′-iodo-[1,1′-biphenyl]-4-carboxylic acid and 4′-cyano-[1,1′-biphenyl]-4-carboxylic acid. The target compound and the intermediates showed no antimicrobial activity against Escherichia coli, Staphylococcus aureus and Candida albicans.

Cuvinte-cheie
Antimicrobial activity, Tetrazole,

Multistep synthesis, Organic ligand, Single crystal X-ray structure

Cerif XML Export

<?xml version='1.0' encoding='utf-8'?>
<CERIF xmlns='urn:xmlns:org:eurocris:cerif-1.5-1' xsi:schemaLocation='urn:xmlns:org:eurocris:cerif-1.5-1 http://www.eurocris.org/Uploads/Web%20pages/CERIF-1.5/CERIF_1.5_1.xsd' xmlns:xsi='http://www.w3.org/2001/XMLSchema-instance' release='1.5' date='2012-10-07' sourceDatabase='Output Profile'>
<cfResPubl>
<cfResPublId>ibn-ResPubl-64942</cfResPublId>
<cfResPublDate>2018-12-05</cfResPublDate>
<cfIssue>1173</cfIssue>
<cfStartPage>63</cfStartPage>
<cfISSN>0022-2860</cfISSN>
<cfURI>https://ibn.idsi.md/ro/vizualizare_articol/64942</cfURI>
<cfTitle cfLangCode='EN' cfTrans='o'>4&prime;-(2H-tetrazol-5-yl)-[1,1&prime;-biphenyl]-4-carboxylic acid: Synthetic approaches, single crystal X-ray structures and antimicrobial activity of intermediates</cfTitle>
<cfKeyw cfLangCode='EN' cfTrans='o'>Antimicrobial activity; Multistep synthesis; Organic ligand; Single crystal X-ray structure; Tetrazole</cfKeyw>
<cfAbstr cfLangCode='EN' cfTrans='o'><p>Two synthetic approaches towards 4&prime;-(2H-tetrazol-5-yl)-[1,1&prime;-biphenyl]-4-carboxylic acid, a valuable organic ligand for the preparation of metal-organic frameworks, are reported. The first reaction sequence leading to the target compound comprises the iodination of [1,1&prime;-biphenyl]-4-carboxylic acid, formation of the methyl ester of 4&prime;-iodo-[1,1&prime;-biphenyl]-4-carboxylic acid, nucleophilic substitution of iodine with cyano, ring closure of tetrazole, and hydrolysis of the ester function. The second synthetic pathway starts from 4-bromobenzonitrile, which is converted through Suzuki coupling with 4-carboxyphenylboronic acid into 4&prime;-cyano-[1,1&prime;-biphenyl]-4-carboxylic acid, which in turn leads to the desired compound after ring closure of tetrazole. All of the synthesized compounds have been fully characterized by IR and <sup>1</sup>H- and <sup>13</sup>C-NMR spectroscopy. Single crystal X-ray structures are reported for the target compound and for methyl esters of 4&prime;-iodo-[1,1&prime;-biphenyl]-4-carboxylic acid and 4&prime;-cyano-[1,1&prime;-biphenyl]-4-carboxylic acid. The target compound and the intermediates showed no antimicrobial activity against Escherichia coli, Staphylococcus aureus and Candida albicans.</p></cfAbstr>
<cfResPubl_Class>
<cfClassId>eda2d9e9-34c5-11e1-b86c-0800200c9a66</cfClassId>
<cfClassSchemeId>759af938-34ae-11e1-b86c-0800200c9a66</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
</cfResPubl_Class>
<cfResPubl_Class>
<cfClassId>e601872f-4b7e-4d88-929f-7df027b226c9</cfClassId>
<cfClassSchemeId>40e90e2f-446d-460a-98e5-5dce57550c48</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
</cfResPubl_Class>
<cfPers_ResPubl>
<cfPersId>ibn-person-58237</cfPersId>
<cfClassId>49815870-1cfe-11e1-8bc2-0800200c9a66</cfClassId>
<cfClassSchemeId>b7135ad0-1d00-11e1-8bc2-0800200c9a66</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
</cfPers_ResPubl>
<cfPers_ResPubl>
<cfPersId>ibn-person-58238</cfPersId>
<cfClassId>49815870-1cfe-11e1-8bc2-0800200c9a66</cfClassId>
<cfClassSchemeId>b7135ad0-1d00-11e1-8bc2-0800200c9a66</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
</cfPers_ResPubl>
<cfPers_ResPubl>
<cfPersId>ibn-person-12182</cfPersId>
<cfClassId>49815870-1cfe-11e1-8bc2-0800200c9a66</cfClassId>
<cfClassSchemeId>b7135ad0-1d00-11e1-8bc2-0800200c9a66</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
</cfPers_ResPubl>
<cfPers_ResPubl>
<cfPersId>ibn-person-28072</cfPersId>
<cfClassId>49815870-1cfe-11e1-8bc2-0800200c9a66</cfClassId>
<cfClassSchemeId>b7135ad0-1d00-11e1-8bc2-0800200c9a66</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
</cfPers_ResPubl>
<cfPers_ResPubl>
<cfPersId>ibn-person-19340</cfPersId>
<cfClassId>49815870-1cfe-11e1-8bc2-0800200c9a66</cfClassId>
<cfClassSchemeId>b7135ad0-1d00-11e1-8bc2-0800200c9a66</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
</cfPers_ResPubl>
<cfPers_ResPubl>
<cfPersId>ibn-person-58239</cfPersId>
<cfClassId>49815870-1cfe-11e1-8bc2-0800200c9a66</cfClassId>
<cfClassSchemeId>b7135ad0-1d00-11e1-8bc2-0800200c9a66</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
</cfPers_ResPubl>
<cfPers_ResPubl>
<cfPersId>ibn-person-12141</cfPersId>
<cfClassId>49815870-1cfe-11e1-8bc2-0800200c9a66</cfClassId>
<cfClassSchemeId>b7135ad0-1d00-11e1-8bc2-0800200c9a66</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
</cfPers_ResPubl>
<cfPers_ResPubl>
<cfPersId>ibn-person-58240</cfPersId>
<cfClassId>49815870-1cfe-11e1-8bc2-0800200c9a66</cfClassId>
<cfClassSchemeId>b7135ad0-1d00-11e1-8bc2-0800200c9a66</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
</cfPers_ResPubl>
<cfFedId>
<cfFedIdId>ibn-doi-64942</cfFedIdId>
<cfFedId>10.1016/j.molstruc.2018.06.086</cfFedId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
<cfFedId_Class>
<cfClassId>31d222b4-11e0-434b-b5ae-088119c51189</cfClassId>
<cfClassSchemeId>bccb3266-689d-4740-a039-c96594b4d916</cfClassSchemeId>
</cfFedId_Class>
<cfFedId_Srv>
<cfSrvId>5123451</cfSrvId>
<cfClassId>eda2b2e2-34c5-11e1-b86c-0800200c9a66</cfClassId>
<cfClassSchemeId>5a270628-f593-4ff4-a44a-95660c76e182</cfClassSchemeId>
</cfFedId_Srv>
</cfFedId>
</cfResPubl>
<cfPers>
<cfPersId>ibn-Pers-58237</cfPersId>
<cfPersName_Pers>
<cfPersNameId>ibn-PersName-58237-3</cfPersNameId>
<cfClassId>55f90543-d631-42eb-8d47-d8d9266cbb26</cfClassId>
<cfClassSchemeId>7375609d-cfa6-45ce-a803-75de69abe21f</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
<cfFamilyNames>Ardeleanu</cfFamilyNames>
<cfFirstNames>Rodinel</cfFirstNames>
</cfPersName_Pers>
</cfPers>
<cfPers>
<cfPersId>ibn-Pers-58238</cfPersId>
<cfPersName_Pers>
<cfPersNameId>ibn-PersName-58238-3</cfPersNameId>
<cfClassId>55f90543-d631-42eb-8d47-d8d9266cbb26</cfClassId>
<cfClassSchemeId>7375609d-cfa6-45ce-a803-75de69abe21f</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
<cfFamilyNames>Dascălu</cfFamilyNames>
<cfFirstNames>Andrei Ioan</cfFirstNames>
</cfPersName_Pers>
</cfPers>
<cfPers>
<cfPersId>ibn-Pers-12182</cfPersId>
<cfPersName_Pers>
<cfPersNameId>ibn-PersName-12182-3</cfPersNameId>
<cfClassId>55f90543-d631-42eb-8d47-d8d9266cbb26</cfClassId>
<cfClassSchemeId>7375609d-cfa6-45ce-a803-75de69abe21f</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
<cfFamilyNames>Shova</cfFamilyNames>
<cfFirstNames>Sergiu</cfFirstNames>
<cfFamilyNames>Шова</cfFamilyNames>
<cfFirstNames>Сергей</cfFirstNames>
</cfPersName_Pers>
</cfPers>
<cfPers>
<cfPersId>ibn-Pers-28072</cfPersId>
<cfPersName_Pers>
<cfPersNameId>ibn-PersName-28072-3</cfPersNameId>
<cfClassId>55f90543-d631-42eb-8d47-d8d9266cbb26</cfClassId>
<cfClassSchemeId>7375609d-cfa6-45ce-a803-75de69abe21f</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
<cfFamilyNames>Nicolescu</cfFamilyNames>
<cfFirstNames>Alina Florica</cfFirstNames>
</cfPersName_Pers>
</cfPers>
<cfPers>
<cfPersId>ibn-Pers-19340</cfPersId>
<cfPersName_Pers>
<cfPersNameId>ibn-PersName-19340-3</cfPersNameId>
<cfClassId>55f90543-d631-42eb-8d47-d8d9266cbb26</cfClassId>
<cfClassSchemeId>7375609d-cfa6-45ce-a803-75de69abe21f</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
<cfFamilyNames>Roşca</cfFamilyNames>
<cfFirstNames>Irina</cfFirstNames>
</cfPersName_Pers>
</cfPers>
<cfPers>
<cfPersId>ibn-Pers-58239</cfPersId>
<cfPersName_Pers>
<cfPersNameId>ibn-PersName-58239-3</cfPersNameId>
<cfClassId>55f90543-d631-42eb-8d47-d8d9266cbb26</cfClassId>
<cfClassSchemeId>7375609d-cfa6-45ce-a803-75de69abe21f</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
<cfFamilyNames>Bratanovici</cfFamilyNames>
<cfFirstNames>Bogdan Ionel</cfFirstNames>
</cfPersName_Pers>
</cfPers>
<cfPers>
<cfPersId>ibn-Pers-12141</cfPersId>
<cfPersName_Pers>
<cfPersNameId>ibn-PersName-12141-3</cfPersNameId>
<cfClassId>55f90543-d631-42eb-8d47-d8d9266cbb26</cfClassId>
<cfClassSchemeId>7375609d-cfa6-45ce-a803-75de69abe21f</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
<cfFamilyNames>Лозан</cfFamilyNames>
<cfFirstNames>В.</cfFirstNames>
</cfPersName_Pers>
</cfPers>
<cfPers>
<cfPersId>ibn-Pers-58240</cfPersId>
<cfPersName_Pers>
<cfPersNameId>ibn-PersName-58240-3</cfPersNameId>
<cfClassId>55f90543-d631-42eb-8d47-d8d9266cbb26</cfClassId>
<cfClassSchemeId>7375609d-cfa6-45ce-a803-75de69abe21f</cfClassSchemeId>
<cfStartDate>2018-12-05T24:00:00</cfStartDate>
<cfFamilyNames>Roman</cfFamilyNames>
<cfFirstNames>Gheorghe</cfFirstNames>
</cfPersName_Pers>
</cfPers>
<cfSrv>
<cfSrvId>5123451</cfSrvId>
<cfName cfLangCode='en' cfTrans='o'>CrossRef DOI prefix service</cfName>
<cfDescr cfLangCode='en' cfTrans='o'>The service of issuing DOI prefixes to publishers</cfDescr>
<cfKeyw cfLangCode='en' cfTrans='o'>persistent identifier; Digital Object Identifier</cfKeyw>
</cfSrv>
</CERIF>