α-Iodonitroalkenes as Potential Antifungal and Antitubercular Agents

被引：6

作者：

Pamarthi, Rambabu ^{[1
,2
]}

Kumar, Ram ^{[3
]}

Sankara, Chennikkayala Siva ^{[4
]}

Lowe, Gabrielle J. ^{[5
]}

Zuegg, Johannes ^{[5
]}

Singh, Sudheer Kumar ^{[3
]}

Ganesh, Madhu ^{[1
,6
]}

机构：

[1] BMS Coll Engn, Dept Chem, Bull Temple Rd, Bengaluru, Karnataka, India

[2] Visveswaraya Technol Univ, Belgaum 590018, Karnataka, India

[3] CSIR Cent Drug Res Inst, Microbiol Div, BS-10-1,Sect-10,Sitapur Rd, Lucknow 226031, Uttar Pradesh, India

[4] Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India

[5] Univ Queensland, Inst Mol Biosci, Community Open Antimicrobial Drug Discovery, 306 Carmody Rd, St Lucia, Qld 4072, Australia

[6] Natl Inst Pharmaceut Educ & Res Hyderabad, Dept Pharmaceut Technol, Balanagar 500037, Telangana, India

来源：

CHEMISTRYSELECT | 2020年 / 5卷 / 39期

关键词：

alpha-iodonitroolefins; Halogenation; Antifungal agents; Drug-resistant Tuberculosis; Drug-resistantC; auris; IN-VITRO EVALUATION; NITROALKENES; CHLORINATION; SUBSTITUENT; RESISTANCE; CONVERSION; RESAZURIN; EFFICIENT; PHICL2; ASSAY;

D O I：

10.1002/slct.202003251

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

beta-Nitrostyrenes undergo one pot sequential addition-elimination reaction when reacted with finely powdered iodine in presence of sodium bicarbonate as base in water and tetrahydrofuran as solvents to afford seventeen alpha-iodonitroalkenes in moderate to good yields (40-88 %). These compounds were tested for activity againstMycobacterium tuberculosisH37Ra and MIC was determined using Rifampicin as positive control. One of the iodo compound14 b, exhibited promising antimycobacterial activity with MIC values of up to 3.125 mu M. Further, twelve alpha-Iodonitroalkenes exhibited significant antifungal activity againstCandida albicans,Cryptococcus neoformansand drug-reistantCandida auris. with MIC values up to <= 0.25 mu M. This opens up the new space in the development of novel pharmacophores for antifungal and antimycobacterial studies.

引用

页码：12272 / 12277

页数：6

共 44 条

[1] Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results [J].

Ballini, R ;

Bosica, G ;

Fiorini, D ;

Palmieri, A ;

Petrini, M .

CHEMICAL REVIEWS, 2005, 105 (03) :933-971

[2] Synthetic Procedures for the Preparation of Nitroalkanes [J].

Ballini, Roberto ;

Palmieri, Alessandro .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (12) :2240-2266

[3] Structure-activity relationship in the 3-iodo-4-phenoxypyridinone (IOPY) series: The nature of the C-3 substituent on anti-HIV activity [J].

Benjahad, Abdellah ;

Oumouch, Said ;

Guillemont, Jerome ;

Pasquier, Elisabeth ;

Mabire, Dominique ;

Andries, Koen ;

Nguyen, Chi Hung ;

Grierson, David S. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (03) :712-716

[4]

Bilich B. E., 1970, ANTIBIOTIKI KIEV, V5, P31

[5] Helping Chemists Discover New Antibiotics [J].

Blaskovich, Mark A. T. ;

Zuegg, Johannes ;

Elliott, Alysha G. ;

Cooper, Matthew A. .

ACS INFECTIOUS DISEASES, 2015, 1 (07) :285-287

[6] Synthesis and monoamine transporter affinity of 3'-analogs of 2-β-carbomethoxy-3-β-(4'-iodophenyl)tropane (β-CIT) [J].

Bois, F ;

Baldwin, RM ;

Kula, NS ;

Baldessarini, RJ ;

Innis, RB ;

Tamagnan, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (09) :2117-2120

[7] Synthesis and biological assay of erlotinib analogues and BSA-conjugated erlotinib analogue [J].

Boobalan, Ramalingam ;

Liu, Kuang-Kai ;

Chao, Jui-I. ;

Chen, Chinpiao .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (08) :1784-1788

[8] The Halogen Bond [J].

Cavallo, Gabriella ;

Metrangolo, Pierangelo ;

Milani, Roberto ;

Pilati, Tullio ;

Priimagi, Arri ;

Resnati, Giuseppe ;

Terraneo, Giancarlo .

CHEMICAL REVIEWS, 2016, 116 (04) :2478-2601

[9] Chlorination of Conjugated Nitroalkenes with PhICl2 and SO2Cl2 for the Synthesis of α-Chloronitroalkenes [J].

Fadeeva, Anastasia A. ;

Ioffe, Sema L. ;

Tabolin, Andrey A. .

SYNTHESIS-STUTTGART, 2020, 52 (18) :2679-2688

[10] Comprehensive analysis of methods used for the evaluation of compounds against Mycobacterium tuberculosis [J].

Franzblau, Scott G. ;

DeGroote, Mary Ann ;

Cho, Sang Hyun ;

Andries, Koen ;

Nuermberger, Eric ;

Orme, Ian M. ;

Mdluli, Khisimuzi ;

Angulo-Barturen, Inigo ;

Dick, Thomas ;

Dartois, Veronique ;

Lenaerts, Anne J. .

TUBERCULOSIS, 2012, 92 (06) :453-488

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