Efficient Multicomponent Approach to the Medicinally Relevant 5-aryl-chromeno[2,3-b]pyridine Scaffold

被引:18
作者
Elinson, Michail N. [1 ]
Vereshchagin, Anatoly N. [1 ]
Anisina, Yuliya E. [1 ]
Egorov, Mikhail P. [1 ]
机构
[1] ND Zelinskii Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia
关键词
2-Aminoprop-1-ene-1; 1; 3-tricarbonitrile; benzaldehyde; catalysis; chromeno[2; 3-b]pyridine; dimedone; multicomponent reaction; NAD(+)-DEPENDENT DNA-LIGASE; ONE-POT SYNTHESIS; 3-COMPONENT SYNTHESIS; ONE-STEP; MALONONITRILE; INHIBITORS; MOLECULES; ALDEHYDES; DESIGN;
D O I
10.1080/10406638.2017.1363062
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The general multicomponent approach was found to the medicinally relevant 5-aryl-chromeno[2,3-b]pyridine scaffold. Triethylamine catalyzed multicomponent reaction of benzaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile and dimedone in a minimal amount of propanol results in efficient formation of substituted 2,4-diamino-8,8-dimethyl-6-oxo-5-aryl-6,7,8,9-tetrahydro-5H-chromeno[2,3-b]pyridine-3-carbonitriles in 75-80% yields. This general and efficient approach avoids traditional recrystallization and chromatographic purification stages and opens a convenient way to scaffolds, promising for many diverse oriented medical applications.
引用
收藏
页码:108 / 115
页数:8
相关论文
共 32 条
[1]   Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2) [J].
Anderson, DR ;
Hegde, S ;
Reinhard, E ;
Gomez, L ;
Vernier, WF ;
Lee, L ;
Liu, S ;
Sambandam, A ;
Snider, PA ;
Masih, L .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (06) :1587-1590
[2]   Cancer chemopreventive effect of phenothiazines and related tri-heterocyclic analogues in the 12-O-tetradecanoylphorbol-13-acetate promoted Epstein-Barr virus early antigen activation and the mouse skin two-stage carcinogenesis models [J].
Azuine, MA ;
Tokuda, H ;
Takayasu, J ;
Enjyo, F ;
Mukainaka, T ;
Konoshima, T ;
Nishino, H ;
Kapadia, GJ .
PHARMACOLOGICAL RESEARCH, 2004, 49 (02) :161-169
[3]   Design, Synthesis and Biological Evaluation of Novel 5H-Chromenopyridines as Potential Anti-Cancer Agents [J].
Banerjee, Souvik ;
Wang, Jin ;
Pfeffer, Susan ;
Ma, Dejian ;
Pfeffer, Lawrence M. ;
Patil, Shivaputra A. ;
Li, Wei ;
Miller, Duane D. .
MOLECULES, 2015, 20 (09) :17152-17165
[4]   Specific and potent inhibition of NAD+-dependent DNA ligase by pyridochromanones [J].
Brötz-Oesterhelt, H ;
Knezevic, I ;
Bartel, S ;
Lampe, T ;
Warnecke-Eberz, U ;
Ziegelbauer, K ;
Häbich, D ;
Labischinski, H .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (41) :39435-39442
[5]   Fast Efficient and General PASE Approach to Medicinally Relevant 4H,5H-Pyrano-[4,3-b]pyran-5-one and 4,6-Dihydro-5H-pyrano-[3,2-c]pyridine-5-one Scaffolds [J].
Elinson, Michail N. ;
Ryzhkov, Fedor V. ;
Nasybullin, Ruslan F. ;
Vereshchagin, Anatoly N. ;
Egorov, Mikhail P. .
HELVETICA CHIMICA ACTA, 2016, 99 (09) :724-731
[6]   Non-catalytic solvent-free synthesis of 5,6,7,8-tetrahydro-4H-chromenes from aldehydes, dimedone and malononitrlie at ambient temperature [J].
Elinson, Michail N. ;
Ryzhkov, Fedor V. ;
Zaimoyskaya, Tatiana A. ;
Egorov, Mikhail P. .
MENDELEEV COMMUNICATIONS, 2015, 25 (03) :185-187
[7]   Solvent-free and 'on-water' multicomponent assembling of aldehydes, 3-methyl-2-pyrazoline-5-one, and malononitrile: fast and efficient approach to medicinally relevant pyrano[2,3-c]pyrazole scaffold [J].
Elinson, Michail N. ;
Nasybullin, Ruslan F. ;
Ryzhkov, Fedor V. ;
Zaimovskaya, Tatiana A. ;
Nikishin, Gennady I. .
MONATSHEFTE FUR CHEMIE, 2015, 146 (04) :631-635
[8]   Chemical and electrocatalytic cascade cyclization of salicylaldehyde with three molecules of malononitrile: 'one-pot' simple and efficient way to the chromeno[2,3-b]pyridine scaffold [J].
Elinson, Michail N. ;
Gorbunov, Sergey V. ;
Vereshchagin, Anatoly N. ;
Nasybullin, Ruslan F. ;
Goloveshkin, Alexander S. ;
Bushmarinov, Ivan S. ;
Egorov, Mikhail P. .
TETRAHEDRON, 2014, 70 (45) :8559-8563
[9]   Solvent-free multicomponent assembling of aldehydes, N,N′-dialkyl barbiturates and malononitrile: fast and efficient approach to pyrano[2,3-d]pyrimidines [J].
Elinson, Michail N. ;
Ryzhkov, Fedor V. ;
Merkulova, Valentina M. ;
Ilovaisky, Alexey I. ;
Nikishin, Gennady I. .
HETEROCYCLIC COMMUNICATIONS, 2014, 20 (05) :281-284
[10]   General approach to spiroacenaphthylene pentacyclic systems: direct multicomponent assembling of acenaphthenequinone and cyclic carbonyl compounds with two molecules of malononitrile [J].
Elinson, Michail N. ;
Ilovaisky, Alexey I. ;
Merkulova, Valentina M. ;
Barba, Fructuoso ;
Batanero, Belen .
TETRAHEDRON, 2013, 69 (34) :7125-7130