Selectivity of N-Aroyl-N′-arylthioureas towards 2-(1,3-Dioxo-1H-inden-2(3H)-ylidene)malononitrile. New Synthesis of (Z)-N-((E)-4-Amino-1-aryl-5-cyano-6-oxo-1H-indeno[1,2-d][1,3]-thiazepin-2(6H)-ylidene)-4-arylamides of Antitumor and Antioxidant Activities

被引:10
|
作者
Aly, Ashraf A. [1 ]
Brown, Alan B. [2 ]
Ramadan, Mohamed [3 ]
Abdel-Aziz, Mohamed [3 ]
Abuo-Rahma, Gamal El-Din A. A. [3 ]
Radwan, Mohamed F. [3 ]
Gamal-Eldeen, Amira M. [4 ]
机构
[1] Menia Univ, Fac Sci, Dept Chem, El Minia 61519, Egypt
[2] Florida Inst Technol, Dept Chem, Melbourne, FL 32901 USA
[3] Menia Univ, Fac Sci, Dept Med Chem, El Minia 61519, Egypt
[4] Natl Res Ctr, Dept Biochem, Div Genet Engn & Biotechnol, Giza, Egypt
关键词
DERIVATIVES;
D O I
10.1002/jhet.344
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction between N-aroyl-M-arylthioureas with 2-(1,3-dioxoindan-2-ylidene)malononitrile furnished indeno[1,2d][1,3]thiazepines in 70-85% yields. The mechanism of the products' formation is discussed. Some of the products showed effective antitumor and antioxidant activities. The results revealed that compound indenothiazepine derivative showed a high inhibition of the cell growth of Hep-G2 cells is compared with the growth of untreated control cells, as concluded from their low 1050 value 21.73 mu M. On the other hand, two indenothiazepine derivatives have an effective antioxidant activity with SC(50) values of 62.5 mM and 87.4 mM, respectively.
引用
收藏
页码:503 / 508
页数:6
相关论文
共 50 条
  • [21] An efficient and facile regioselective synthesis of new substituted (E)-1-(3-aryl-7,8-dihydrocinnoline-5(6H)-ylidene)hydrazines and (1E,2E)-1,2-bis(3-aryl-7,8-dihydrocinnoline-5(6H)-ylidene)hydrazines
    Khalafy, Jabbar
    Ezzati, Mahnaz
    Rimaz, Mehdi
    Marjani, Ahmad Poursattar
    Asl, Hooman Yaghoobnejad
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2014, 11 (04) : 1067 - 1074
  • [22] An efficient and facile regioselective synthesis of new substituted (E)-1-(3-aryl-7,8-dihydrocinnoline-5(6H)-ylidene)hydrazines and (1E,2E)-1,2-bis(3-aryl-7,8-dihydrocinnoline-5(6H)-ylidene)hydrazines
    Jabbar Khalafy
    Mahnaz Ezzati
    Mehdi Rimaz
    Ahmad Poursattar Marjani
    Hooman Yaghoobnejad Asl
    Journal of the Iranian Chemical Society, 2014, 11 : 1067 - 1074
  • [23] 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
    Kochia, Khudaidad
    Bayat, Mohammad
    Nasri, Shima
    Mohammadi, Aref
    MOLECULAR DIVERSITY, 2020, 24 (04) : 1015 - 1024
  • [24] 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
    Khudaidad Kochia
    Mohammad Bayat
    Shima Nasri
    Aref Mohammadi
    Molecular Diversity, 2020, 24 : 1015 - 1024
  • [25] Electrocatalytic trimerization of N,N′-dialkylbarbituric acids: facile and efficient way to 2′H-5,5′:5′,5"-terpyrimidine-2,2′,2",4,4′,4",6,6′,6"-(1H,1′H,1"H,3H,3′H,3"H,5H,5"H)-nonone framework
    Vereshchagin, Anatoly N.
    Elinson, Michail N.
    Dorofeeva, Evgeniya O.
    Bushmarinov, Ivan S.
    Gorbunov, Sergey V.
    Belyakov, Pavel A.
    Chizhov, Alexander O.
    Nikishin, Gennady I.
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2012, 363 : 69 - 73
  • [26] 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
    Sepay, Nayim
    Mallik, Sumitava
    Guha, Chayan
    Mallik, Asok K.
    RSC ADVANCES, 2016, 6 (98) : 96016 - 96024
  • [27] Synthesis and Study the Antimicrobial Activity of Novel 2-(1H-indol-3-yl)-N-(3, 4-diphenylthiazol-2(3H)-ylidene) Ethanamine Derivatives
    Kumbhare, Ravindra M.
    Kumar, K. Vijay
    Dadmal, Tulshiram L.
    Kosurkar, Umesh B.
    Appalanaidu, K.
    MEDICINAL CHEMISTRY, 2013, 9 (02) : 287 - 293
  • [28] Two-step novel synthesis of 2-amino-6-(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-4,7-diphenyloxepine-3-carbonitrile and 5-(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-2-imino-6-phenyl-2H-pyran-3-carbonitrile
    Abou Elmaaty, Tarek M.
    SYNTHETIC COMMUNICATIONS, 2006, 36 (16) : 2281 - 2285
  • [29] 5-Methyl-N'-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-ylidene]-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide
    Mohamed, Hanan A.
    Abdel-Wahab, Bakr F.
    Ng, Seik Weng
    Tiekink, Edward R. T.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O577 - +
  • [30] A unique synthesis of N-(Z)-5-bromo-6-hydroxyhexahydro isobenzofuran-1(3H)-ylidene)methanaminium bromide
    Özlem Gündoğdu
    Ertan Şahin
    Yunus Kara
    Chemical Papers, 2024, 78 : 1347 - 1352