Synthesis of New Hybrid Molecules Based on Isomerically Pure 5Z,9Z-Alkadienoic Acids and Monocarbonyl Curcumin Analog

被引:0
作者
Islamov, I. I. [1 ]
Yusupova, A. V. [1 ]
D'yakonov, V. A. [2 ]
Dzhemilev, U. M. [2 ]
机构
[1] Russian Acad Sci, Inst Petrochem & Catalysis, Ufa Fed Res Ctr, Ufa 450075, Russia
[2] Russian Acad Sci, Zelinsky Inst Organ Chem, Moscow 119991, Russia
关键词
metal complex catalysis; cross-cyclomagnesiation; Grignard reagents; fatty acids; curcuminoids; HUMAN TOPOISOMERASE-I; STABILITY; CHEMISTRY; DESIGN; AGENTS;
D O I
10.1134/S1070428022120272
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Previously unknown hybrid compounds based on monocarbonyl curcumin analog and long-chain (5Z,9Z)-alka-5,9-dienoic acids were synthesized for the first time in 61-67% yields. The required unsaturated acids were prepared via Cp2TiCl2-catalyzed stereoselective intermolecular cross-cyclomagnesiation of aliphatic 1,2-dienes and 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran as the key step.
引用
收藏
页码:1963 / 1968
页数:6
相关论文
共 35 条
[1]   Anticancer Activity of Curcumin and Its Analogues: Preclinical and Clinical Studies [J].
Allegra, Alessandro ;
Innao, Vanessa ;
Russo, Sabina ;
Gerace, Demetrio ;
Alonci, Andrea ;
Musolino, Caterina .
CANCER INVESTIGATION, 2017, 35 (01) :1-22
[2]   Bioavailability of curcumin: Problems and promises [J].
Anand, Preetha ;
Kunnumakkara, Ajaikumar B. ;
Newman, Robert A. ;
Aggarwal, Bharat B. .
MOLECULAR PHARMACEUTICS, 2007, 4 (06) :807-818
[3]   Curcumin Therapeutic Modulation of the Wnt Signaling Pathway [J].
Ashrafizadeh, Milad ;
Ahmadi, Zahra ;
Mohamamdinejad, Reza ;
Yaribeygi, Habib ;
Serban, Maria-Corina ;
Orafai, Hossein M. ;
Sahebkar, Amirhossein .
CURRENT PHARMACEUTICAL BIOTECHNOLOGY, 2020, 21 (11) :1006-1015
[4]   Recent developments in chemistry and biology of curcumin analogues [J].
Bairwa, Khemraj ;
Grover, Jagdeep ;
Kania, Mihir ;
Jachak, Sanjay M. .
RSC ADVANCES, 2014, 4 (27) :13946-13978
[5]   Monocarbonyl analogs of curcumin inhibit growth of antibiotic sensitive and resistant strains of Mycobacterium tuberculosis [J].
Baldwin, Patrick R. ;
Reeves, Analise Z. ;
Powell, Kimberly R. ;
Napier, Ruth J. ;
Swimm, Alyson I. ;
Sun, Aiming ;
Giesler, Kyle ;
Bommarius, Bettina ;
Shinnick, Thomas M. ;
Snyder, James P. ;
Liotta, Dennis C. ;
Kalman, Daniel .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 :693-699
[6]   Natural compounds with bis-methylene-interrupted Z-double bonds: plant sources, strategies of total synthesis, biological activity, and perspectives [J].
D'yakonov, Vladimir A. ;
Dzhemileva, Lilya U. ;
Dzhemilev, Usein M. .
PHYTOCHEMISTRY REVIEWS, 2021, 20 (01) :325-342
[7]   Catalytic cyclometallation in steroid chemistry V: Synthesis of hybrid molecules based on steroid oximes and (5Z,9Z)-tetradeca-5,9-dienedioic acid as potential anticancer agents [J].
D'yakonov, Vladimir A. ;
Tuktarova, Regina A. ;
Dzhemileva, Lilya U. ;
Ishmukhametova, Svetlana R. ;
Yunusbaeva, Milyausha M. ;
Dzhemilev, Usein M. .
STEROIDS, 2018, 138 :14-20
[8]   nZ,(n+4) Z-Dienoic fatty acids: a new method for the synthesis and inhibitory action on topoisomerase I and IIα [J].
D'yakonov, Vladimir A. ;
Dzhemileva, Lilya U. ;
Makarov, Aleksey A. ;
Mulyukova, Alfiya R. ;
Baev, Dmitry S. ;
Khusnutdinova, Elza K. ;
Tolstikova, Tatiana G. ;
Dzhemilev, Usein M. .
MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (01) :30-39
[9]   Catalytic cyclometallation in steroid chemistry III1 : Synthesis of steroidal derivatives of 5Z,9Z-dienoic acid and investigation of its human topoisomerase I inhibitory activity [J].
D'yakonov, Vladimir A. ;
Dzhemileva, Lilya U. ;
Tuktarova, Regina A. ;
Makarov, Aleksey A. ;
Islamov, Ilgiz I. ;
Mulyukova, Alfiya R. ;
Dzhemilev, Usein M. .
STEROIDS, 2015, 102 :110-117
[10]   Stereoselective synthesis of 11-phenylundeca-5Z,9Z-dienoic acid and investigation of its human topoisomerase I and IIα inhibitory activity [J].
D'yakonov, Vladimir A. ;
Dzhemileva, Lilya U. ;
Makarov, Aleksey A. ;
Mulukova, Alfiya R. ;
Baev, Dmitry S. ;
Khusnutdinova, Elza K. ;
Tolstikova, Tatiana G. ;
Dzhemilev, Usein M. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (11) :2405-2408