An efficient synthesis of 1,3-dimethyl-5-(2-phenyl-4H-chromen-4-ylidene) pyrimidine-2,4,6(1H,3H,5H)-triones and investigation of their interactions with β-lactoglobiulin

被引：22

作者：

Sepay, Nayim ^{[1
]}

Mallik, Sumitava ^{[1
]}

Guha, Chayan ^{[1
]}

Mallik, Asok K. ^{[1
]}

机构：

[1] Jadavpur Univ, Dept Chem, Kolkata 700032, India

来源：

RSC ADVANCES | 2016年 / 6卷 / 98期

关键词：

THROUGHPUT SCREENING ASSAY; PUSH-PULL; BARBITURIC-ACID; BINDING; CHROMENES; DISCOVERY; APOPTOSIS; 4-ARYL-4H-CHROMENES; DERIVATIVES; ALKYLATION;

D O I：

10.1039/c6ra13584f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient method for synthesis of 1,3-dimethyl-5-(2-phenyl-4H-chromen-4-ylidene) pyrimidine-2,4,6( 1H,3H,5H)-triones has been developed by treatment of 2-hydroxychalcones and 1,3-dimethylbarbituric acid in refluxing toluene in the presence of amberlyst-15 as catalyst in air. The process involves the occurrence of a domino sequence of Michael addition, cyclization and aerial oxidation. The compounds synthesized showed an interesting property of free rotation around the bond linking the two heterocyclic moieties and three of them were found to show binding property with the milk protein beta-lactoglobulin (beta-lg) DFT and docking (with beta-lg) studies of one of the compounds have been done.

引用

页码：96016 / 96024

页数：9

共 50 条

[41] Reaction 5-(Arylmethylidene)-2,4,6-pyrimidine-2,4,6(1H,3H,5H)-triones with Arenecarbaldehyde Phenylhydrazones in the Presence of Sodium N-Chlorobenzenesulfonamide
Tyrkov, A. G.
Yurtaeva, E. A.
Rsaeva, O. B.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (02) : 269 - 272
[42] 5-(Arylmethylidene)-2,4,6-pyrimidine-2,4,6(1H,3H,5H)-triones in Reaction with p-Phenacyl- and p-Acetonylisoquinolinium bromides
Tyrkov, A. G.
Nosachev, S. B.
Vladimirova, T. S.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (05) : 762 - 765
[43] Reaction 5-(Arylmethylidene)-2,4,6-pyrimidine-2,4,6(1H,3H,5H)-triones with Arenecarbaldehyde Phenylhydrazones in the Presence of Sodium N-Chlorobenzenesulfonamide
A. G. Tyrkov
E. A. Yurtaeva
O. B. Rsaeva
Russian Journal of Organic Chemistry, 2019, 55 : 269 - 272
[44] Synthesis and evaluation of substituted 5-(3-chloro-2-oxo-4-phenylazetidin-1-ylamino)pyrimidine-2,4,6(1H,3H,5H)-triones against pentylenetetrazole-induced convulsant in mice
Karan Deep Singh Puri
Shailja Sood
Arunachalam Muthuraman
Medicinal Chemistry Research, 2012, 21 : 2300 - 2306
[45] Synthesis and evaluation of substituted 5-(3-chloro-2-oxo-4-phenylazetidin-1-ylamino)pyrimidine-2,4,6(1H,3H,5H)-triones against pentylenetetrazole-induced convulsant in mice
Puri, Karan Deep Singh
Sood, Shailja
Muthuraman, Arunachalam
MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (09) : 2300 - 2306
[46] 5-[1-(1,3-Dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)-2-oxopropyl]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)trione
Sweidan, Kamal
Steimann, Manfred
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1334 - +
[47] Crystal structure of 5-(2,6-dimethyl-4H-pyran-4-ylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C13H14N2O4
Li, Xiaochuan
Li, Yajuan
Zhang, Junna
Son, Young-A
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2013, 228 (01): : 97 - 98
[48] Synthesis and Electrical and Gas Sensing Properties of Some 5-(Quinolinylmethylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione and 5-(Quinolinylmethylene)pyrimidine-2,4,6(1H,3H,5H)-trione Derivatives
Beker, H. Kerim
Canlica, Mevlude
Akinci, Alper
Altindal, Ahmet
Kaban, Seniz
JOURNAL OF CHEMISTRY, 2013, 2013
[49] Synthesis of Phosphorus, Arsenic and Antimony Ylides Containing the 1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione Fragments
Sweidan, Kamal
Al-Sheikh, Ahmed
Sweileh, Bassam
Sunjuk, Mahmoud
Kuhn, Norbert
LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (01) : 1 - 3
[50] Synthesis and antimicrobial activity of novel imidazo[1,2-a]pyridinopyrimidine-2,4,6(1H,3H,5H)-triones and thioxopyrimidine-4,6(1H,5H)diones
G. Rajitha
V. Ravibabu
G. Ramesh
B. Rajitha
Research on Chemical Intermediates, 2016, 42 : 1989 - 1998

← 1 2 3 4 5 →