Synthesis, Characterization, and Antifungal Activity of Some New Thieno[2,3-b]pyridines Incorporating Quinazoline or Benzimidazole Moiety

被引：6
作者：
Ibrahim, O. F. [1 ]
Bakhite, E. A. [1 ]
Metwally, S. A. M. [1 ]
El-Ossaily, Y. A. [1 ,2 ]
Abdu-Allah, H. H. M. [3 ]
Al-Taifi, E. A. [4 ]
Kandel, M. [5 ,6 ]
机构：
[1] Assiut Univ, Fac Sci, Dept Chem, Assiut 71515, Egypt
[2] Jouf Univ, Coll Sci, Chem Dept, Sakaka 2014, Saudi Arabia
[3] Assiut Univ, Fac Pharm, Dept Pharmaceut Organ Chem, Assiut 71515, Egypt
[4] Sanaa Univ, Fac Sci, Dept Chem, Sanaa, Yemen
[5] King Faisal Univ, Coll Vet Med, Dept Biomed Sci, Al Hasa 31982, Saudi Arabia
[6] Kafrelsheikh Univ, Fac Vet Med, Dept Pharmacol, Kafrelsheikh 33516, Egypt
来源：
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY | 2021年 / 47卷 / 04期
关键词：
synthesis; antifungal activity; thienopyridines; quinazolines; BIOLOGICAL EVALUATION; THIENOPYRIDINE DERIVATIVES; PYRIDOTHIENOPYRIMIDINES; PYRIDINE;
D O I：
10.1134/S1068162021040117
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：
Reaction of 4,6-dimethyl-3-cyanopyridine-2(1H)-thione (IIIa) or 4,5,6-trisubstituted-3-cyanopyridine-2(1H)-thiones (IIIb-d) with 2-chloromethylquinazoline-4(3H)-one (IVa) furnished the corresponding 3-amino-2-(4-oxo-3,4-dihydroquinazolin-2-yl)thieno[2,3-b]pyridines (VIa-d). Reaction of aminothieno-pyridines (VIa, b, d) were reacted with triethyl orthoformate, acetic anhydride or nitrous acid to furnish pyridothienopyrimidoquinazolines (VIIIa, b, d), (IXa, b, d) or pyridothienotriazinoquinazolines (Xa, b, d). The new compound, 3-cyano-5-acetyl-6-methyl-4-styrylpyridine-2(1H)-thione (IIIe) was synthesized and reacted with 2-chloromethyl-1H-benzimadazole to give 5-acetyl-3-amino-2-(1H-benzimidazol-2-yl)-6-methyl-4-styryl-thieno[2,3-b]pyridine (XII) which was used as a key intermediate for synthesizing pyridothienopyrimidobenzimidazoles (XIII, XIV). All newly synthesized compounds were characterized on the basis of their elemental and spectral analyses. Also, most of the synthesized compounds were screened in vitro for their antifungal activity.
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页码：918 / 928
页数：11
相关论文
共 47 条
[1]  
Abdel Hamide S.G., 2006, J SAUDI CHEM SOC, V10, P1131
[2]  
Abdel-Rahman AE, 2003, PHARMAZIE, V58, P372
[3]   Eco-friendly synthesis of novel cyanopyridine derivatives and their anticancer and PIM-1 kinase inhibitory activities [J].
Abouzid, Khaled A. M. ;
Al-Ansary, Ghada H. ;
El-Naggar, Abeer M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 134 :357-365
[4]  
Altaf A.A., 2015, A Review on the Medicinal Importance of Pyridine Derivatives, V1, P1, DOI [DOI 10.11648/J.JDDMC.20150101.11, https://doi.org/10.11648/j.jddmc.20150101.11]
[5]  
Anand PRV, 2009, ASIAN J CHEM, V21, P6656
[6]   Reactions with cyanothioacetamide and its derivatives: Synthesis and characterization of several new pyridine and annelated pyridine derivatives [J].
Attaby, FA ;
Eldin, SM ;
Basouni, WM ;
Elneairy, MAA .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 108 (1-4) :31-39
[7]   Synthesis, reactions, and antiviral activity of 6′-amino-2′-thioxo-1′,2′-dihydro-3,4′-bipyridine-3′,5′-dicarbonitrile [J].
Attaby, Fawzy A. ;
Elghandour, A. H. H. ;
Ali, M. A. ;
Ibrahem, Yasser M. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (04) :695-709
[8]   Synthesis and antidiabetic activity of 2,5-disubstituted-3-imidazol-2-yl-pyrrolo[2,3-b]pyridines and thieno[2,3-b]pyridines [J].
Bahekar, Rajesh H. ;
Jain, Mukul R. ;
Jadav, Pradip A. ;
Prajapati, Vijay M. ;
Patel, Dipam N. ;
Gupta, Arun A. ;
Sharma, Ajay ;
Tom, Robby ;
Bandyopadhya, Debdutta ;
Modi, Honey ;
Patel, Pankaj R. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (21) :6782-6795
[9]   Recent trends in the chemistry of thienopyridines [J].
Bakhite, EAG .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (05) :929-992
[10]   Pyridine derivatives as insecticides. Part 2: Synthesis of some piperidinium and morpholinium cyanopyridinethiolates and their insecticidal activity [J].
Bakhite, Etify A. ;
Abd-Ella, Aly A. ;
El-Sayed, Mohamed E. A. ;
Abdel-Raheem, Shaban A. A. .
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2017, 21 (01) :95-104
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