Synthesis and cytotoxicity of (R)- and (S)-ricinoleic acid amides and their acetates

被引：11

作者：

Matysiak, Sylwia ^{[1
]}

Chmiel, Agnieszka ^{[2
]}

Skolimowski, Janusz ^{[3
]}

Kula, Jozef ^{[1
]}

Pasternak, Beata ^{[4
]}

Blaszczyk, Alina ^{[2
]}

机构：

[1] Lodz Univ Technol, Inst Gen Food Chem, Fac Biotechnol & Food Sci, Lodz, Poland

[2] Univ Lodz, Fac Biol & Environm Protect, Dept Gen Genet Mol Biol & Plant Biotechnol, Lab Cytogenet, Banacha 12-16, PL-90237 Lodz, Poland

[3] Univ Rzeszow, Fac Biol & Agr, Dept Analyt Biochem, Rzeszow, Poland

[4] Univ Lodz, Dept Organ Chem, Fac Chem, Lodz, Poland

来源：

CHIRALITY | 2017年 / 29卷 / 10期

关键词：

cytotoxicity; ethanolamine; fatty acid amides; methyl ricinoleates; MTT assay; pyrrolidine; RICINOLEIC ACID; DERIVATIVES;

D O I：

10.1002/chir.22733

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An environment-friendly, free of solvent, process for the synthesis of (R)- and (S)-ricinoleic acid amides has been developed. Starting from methyl ricinoleates and pyrrolidine or ethanolamine, the corresponding amides were obtained with yields ranging from 83-88%. Among 12 synthesized derivatives of ricinoleic acid, including the starting methyl esters, amides, and their acetates, nine compounds were obtained and tested for the first time. Studies on ricinoleic acid derivatives cytotoxicity showed that methyl esters were the least cytotoxic compounds and modification of their structure resulted in increasing cytotoxicity of the obtained products against both cancer cells and normal lymphocytes. Both enantiomers of the ethanolamine-derived amides showed the most promising anticancer potential.

引用

页码：616 / 622

页数：7

共 22 条

[1] Development of the first ultra-potent "capsaicinoid" agonist at transient receptor potential vanilloid type 1 (TRPV1) channels and its therapeutic potential [J].

Appendino, G ;

De Petrocellis, L ;

Trevisani, M ;

Minassi, A ;

Daddario, N ;

Moriello, AS ;

Gazzieri, D ;

Ligresti, A ;

Campi, B ;

Fontana, G ;

Pinna, C ;

Geppetti, P ;

Di Marzo, V .

JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2005, 312 (02) :561-570

[2] Novel α-hydroxy phosphonic acids via castor oil [J].

Cermak, Diana M. ;

Cermak, Steven C. ;

Deppe, Amy B. ;

Durham, Amber L. .

INDUSTRIAL CROPS AND PRODUCTS, 2012, 37 (01) :394-400

[3] Antiproliferative activity of synthetic fatty acid amides from renewable resources [J].

dos Santos, Daiane S. ;

Piovesan, Luciana A. ;

D'Oca, Caroline R. Montes ;

Hack, Carolina R. Lopes ;

Treptow, Tamara G. M. ;

Rodrigues, Marieli O. ;

Vendramini-Costa, Debora B. ;

Ruiz, Ana Lucia T. G. ;

de Carvalho, Joao Ernesto ;

Montes D'Oca, Marcelo G. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (02) :340-347

[4] Fatty acid amide signaling molecules [J].

Ezzili, Cyrine ;

Otrubova, Katerina ;

Boger, Dale L. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (20) :5959-5968

[5] Biosynthesis, degradation and pharmacological importance of the fatty acid amides [J].

Farrell, Emma K. ;

Merkler, David J. .

DRUG DISCOVERY TODAY, 2008, 13 (13-14) :558-568

[6] Plasma levels of lidocaine, o-toluidine, and prilocaine after application of 8.5 g Oraqix® in patients with generalized periodontitis:: effect on blood methemoglobin and tolerability [J].

Herdevall, BM ;

Klinge, B ;

Persson, L ;

Huledal, G ;

Abdel-Rehim, M .

ACTA ODONTOLOGICA SCANDINAVICA, 2003, 61 (04) :230-234

[7] Synthesis of enantiomerically pure volatile compounds derived from (R)-3-hydroxynonanal [J].

Kula, J ;

Quang, TB ;

Sikora, M .

TETRAHEDRON-ASYMMETRY, 2000, 11 (04) :943-950

[8] Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid [J].

Kula, Jozef ;

Bonikowski, Radoslaw ;

Szewczyk, Malgorzata ;

Ciolak, Kornelia .

CHEMISTRY AND PHYSICS OF LIPIDS, 2014, 183 :137-141

[9] Synthesis and antibacterial activity of ricinoleic acid glycosides [J].

Kuppala, Ramakrishna ;

Govindarajan, Mugunthan ;

Tambat, Rushikesh ;

Patel, Neeraj ;

Nandanwar, Hemraj ;

Bhutani, Kamlesh K. ;

Kartha, K. P. Ravindranathan .

RSC ADVANCES, 2016, 6 (05) :3700-3713

[10] SYNTHESIS OF NEW FATTY ACIDS AMIDES FROM AMINOLYSIS OF FAMES [J].

Lopes, Carolina R. ;

Montes D'Oca, Caroline Da Ros ;

Duarte, Rodrigo da C. ;

Kurz, Marcia H. S. ;

Prime, Ednei G. ;

Clementin, Rosilene M. ;

Villarreyes, Joaquin Ariel M. ;

Montes D'Oca, Marcelo G. .

QUIMICA NOVA, 2010, 33 (06) :1335-1341

← 1 2 3 →