Synthesis of New Derivatives of 3-Aryl-1,5-dimethyl-1H-[1,2,4]triazolo[4′,3′:1,2]pyrimido[4,5-e][1,3,4]oxadiazines as Potential Antiproliferative Agents

被引:17
作者
Bakavoli, Mehdi [1 ]
Rahimizadeh, Mohammad [1 ]
Shiri, Ali [1 ]
Akbarzadeh, Marzieh [1 ]
Mousavi, Seyed-Hadi [2 ,3 ,4 ]
Tayarani-Najaran, Zahra [2 ,3 ]
Atapour-Mashhad, Hoda [4 ,5 ]
Nikpour, Mohsen [6 ]
机构
[1] Ferdowsi Univ Mashhad, Sch Sci, Dept Chem, Mashhad 917751436, Iran
[2] Mashhad Univ Med Sci, Sch Med, Dept Pharmacol, Mashhad, Iran
[3] Mashhad Univ Med Sci, Sch Med, Pharmacol Res Ctr Med Plants, Mashhad, Iran
[4] Mashhad Univ Med Sci, Med Toxicol Res Ctr, Mashhad, Iran
[5] PNU, Dept Chem, Mashhad, Iran
[6] Islamic Azad Univ, Ahvaz Branch, Sch Sci, Dept Chem, Ahvaz, Iran
关键词
HETEROCYCLIC-COMPOUNDS; FACILE SYNTHESIS; ANTIBACTERIAL; HYDRAZONES;
D O I
10.1002/jhet.509
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Starting from pyrimido[4,5-e][1,3,4]oxadiazines (3a-c), a synthetic pathway to [1,2,4]triazolo[4',3':1,2]pyrimido[4,5-e][1,3,4]oxadiazines (5a-i) is described. The reaction of pyrimido[4,5-e][1,3,4]oxadiazines (3a-c) with hydrazine hydrate afforded the corresponding hydrazino derivatives (4a-c). Further treatment of these compounds with different orthoesters in acetic acid gave the corresponding [1,2,4]triazolo[4',3':1,2]pyrimido[4,5-e][1,3,4]oxadiazines (5a-i). Compound (3a) and (5b), as examples, were tested on different cancer cell lines including He La, MCF-7, and HepG2. Malignant cells were cultured in DMEM medium and incubated with different concentrations of the titled compounds. Cell viability was quantitated by MTT assay.
引用
收藏
页码:183 / 187
页数:5
相关论文
共 36 条
[1]   Reaction of hydrazonoyl halides 51:: A facile synthesis of 5-arylthiazoles and triazolino[4,3-a]pyrimidines as antimicrobial agents [J].
Abdelhamid, Abdou O. ;
Sayed, Abdelwahed R. ;
Zaki, Yasser H. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (07) :1447-1457
[2]   Design and synthesis of pyrimido[4,5-b][1,4]benzothiazine derivatives, as potent 15-lipoxygenase inhibitors [J].
Bakavoli, M. ;
Nikpour, M. ;
Rahimizadeh, M. ;
Saberi, M. R. ;
Sadeghian, H. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (05) :2120-2126
[3]   New access to thiazolo[4,5-d]pyrimidine derivatives [J].
Bakavoli, M. ;
Nikpour, M. ;
Rahimizadeh, M. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (05) :1327-1329
[4]   Investigation into the regioisomeric composition of some fused pyrimidines: 1H NMR and theoretical studies [J].
Bakavoli, M. ;
Raissi, H. ;
Tajabadi, J. ;
Karimi, M. ;
Davoodnia, A. ;
Nikpour, M. .
JOURNAL OF SULFUR CHEMISTRY, 2008, 29 (01) :25-30
[5]   Facile synthesis of 2-anilinopyrimido [4,5-e][1,3,4]thiadiazines [J].
Bakavoli, Mehdi ;
Rahimizadeh, Mohammad ;
Shiri, Ali ;
Eshghi, Hossein ;
Nickpour, Mohsen .
HETEROCYCLES, 2008, 75 (07) :1745-1748
[6]   SAR comparative studies on pyrimido[4,5-b][1,4] benzothiazine derivatives as 15-lipoxygenase inhibitors, using ab initio calculations [J].
Bakavoli, Mehdi ;
Sadeghian, Hamid ;
Tabatabaei, Zahra ;
Rezaei, Elham ;
Rahimizadeh, Mohammad ;
Nikpour, Mohsen .
JOURNAL OF MOLECULAR MODELING, 2008, 14 (06) :471-478
[7]   Synthesis and Antibacterial Evaluations of New Pyridazino-[4,3-e][1,3,4]oxadiazines [J].
Bakavoli, Mehdi ;
Rahimizadeh, Mohammad ;
Shiri, Ali ;
Eshghi, Hossein ;
Pordeli, Parvaneh ;
Pordel, Mehdi ;
Nikpour, Mohsen .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (01) :149-152
[8]   Molecular iodine promoted synthesis of new pyrazolo[3,4-d]pyrimidine derivatives as potential antibacterial agents [J].
Bakavoli, Mehdi ;
Bagherzadeh, Ghodsieh ;
Vaseghifar, Maryam ;
Shiri, Ali ;
Pordel, Mehdi ;
Mashreghi, Mansour ;
Pordeli, Parvaneh ;
Araghi, Maryam .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) :647-650
[9]   Iodine catalysed synthesis and antibacterial evaluation of thieno[2,3-d] pyrimidine derivatives [J].
Bakavoli, Mehdi ;
Bagherzadeh, Ghodsieh ;
Vaseghifar, Maryam ;
Shiri, Ali ;
Pordeli, Parvaneh .
JOURNAL OF CHEMICAL RESEARCH-S, 2009, (11) :653-655
[10]   Antimicrobial and antitumor activity of N-heteroimmine-1,2,3-dithiazoles and their transformation in triazolo-, imidazo-, and pyrazolopirimidines [J].
Baraldi, PG ;
Pavani, MG ;
Nuñez, MD ;
Brigidi, P ;
Vitali, B ;
Gambari, R ;
Romagnoli, R .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (02) :449-456