Synthesis of new pyrimidine-containing compounds: 5-(2-(alkylamino)-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-6-hydroxypyrimidine-2,4(1H,3H)-dione derivatives

被引:3
作者
Kochia, Khudaidad [1 ]
Bayat, Mohammad [1 ]
Nasri, Shima [1 ]
Mohammadi, Aref [1 ]
机构
[1] Imam Khomeini Int Univ, Fac Sci, Dept Chem, Qazvin, Iran
关键词
Pyrimidine; Barbituric acid; Ninhydrin; Nitroketene dithioacetals; Indene; PHARMACOKINETICS; DESIGN; ANTIOXIDANT; NINHYDRIN;
D O I
10.1007/s11030-019-10009-w
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In this study, the one-pot reaction between primary amines, 1,1-bis-(methylthio)-2-nitroethene, ninhydrin, and barbituric acid as an enolizable C-H-activated compound provides a simple method for the preparation of 5-(2-(alkylamino)-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-6-hydroxypyrimidine-2,4(1H,3H)-dione derivatives with potential synthetic and pharmacological interest. This reaction shows attractive characteristics, such as substrate availability, good yields, existence of numerous hydrogen-bonding possibilities in product, and its mild conditions in ethanol media. Graphic abstract
引用
收藏
页码:1015 / 1024
页数:10
相关论文
共 33 条
[1]  
Abu-Hashem AA, 2010, ACTA PHARMACEUT, V60, P311, DOI 10.2478/v10007-010-0030-y
[2]  
Ahmed N, 2016, STUD NAT PROD CHEM, V51, P383, DOI 10.1016/B978-0-444-63932-5.00008-5
[3]  
Ajani O.O., 2015, INT J BIOL CHEM, V9, P148, DOI [10.3923/ijbc.2015.148.177, DOI 10.3923/IJBC.2015.148.177]
[4]   A Novel and One-Pot Multicomponent Approach to the Synthesis of Dihyroindeno[1,2-b]pyrroles and Indeno[2′,1′:4,5]pyrrolo[1,2-a]-Fused 1,3-Diazaheterocycles [J].
Alizadeh, Abdolali ;
Zarei, Ameneh ;
Rezvanian, Atieh .
SYNTHESIS-STUTTGART, 2011, (03) :497-501
[5]   Bicyclic pyrimidine nucleoside analogues (BCNAs) as highly selective and potent inhibitors of varicella-zoster virus replication [J].
Balzarini, J ;
McGuigan, C .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2002, 50 (01) :5-9
[6]  
Basavaraj HS, 2005, INDIAN J HETEROCY CH, V15, P69
[7]   TRIMETHOPRIM - A REVIEW OF ITS ANTIBACTERIAL ACTIVITY, PHARMACOKINETICS AND THERAPEUTIC USE IN URINARY-TRACT INFECTIONS [J].
BROGDEN, RN ;
CARMINE, AA ;
HEEL, RC ;
SPEIGHT, TM ;
AVERY, GS .
DRUGS, 1982, 23 (06) :405-430
[8]   Design, synthesis and biological evaluation of indane-2-arylhydrazinylmethylene-1,3-diones and indol-2-aryldiazenylmethylene-3-ones as β-amyloid aggregation inhibitors [J].
Catto, Marco ;
Aliano, Rosaria ;
Carotti, Angelo ;
Cellamare, Saverio ;
Palluotto, Fausta ;
Purgatorio, Rosa ;
De Stradis, Angelo ;
Campagna, Francesco .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (04) :1359-1366
[9]   A divergent synthetic pathway for pyrimidine-embedded medium-sized azacycles through an N-quaternizing strategy [J].
Choi, Yoona ;
Kim, Heejun ;
Park, Seung Bum .
CHEMICAL SCIENCE, 2019, 10 (02) :569-575
[10]  
El-Kanzi NAA, 2013, HETEROCYCL LETT, V3, P81