Synthesis and Evaluation of New 1,5-Diaryl-3-[4-(methyl-sulfonyl)phenyl]-4,5-dihydro-1H-pyrazole Derivatives as Potential Antidepressant Agents

被引:66
|
作者
Ozdemir, Ahmet [1 ]
Altintop, Mehlika Dilek [1 ,2 ]
Kaplancikli, Zafer Asim [1 ]
Can, Ozgur Devrim [3 ]
Ozkay, Umide Demir [3 ]
Turan-Zitouni, Gulhan [1 ]
机构
[1] Anadolu Univ, Dept Pharmaceut Chem, Fac Pharm, TR-26470 Eskisehir, Turkey
[2] Anadolu Univ, Grad Sch Hlth Sci, TR-26470 Eskisehir, Turkey
[3] Anadolu Univ, Dept Pharmacol, Fac Pharm, TR-26470 Eskisehir, Turkey
关键词
TAIL SUSPENSION TEST; INVOLVEMENT; DESIGN;
D O I
10.3390/molecules20022668
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 an effort to develop potent antidepressant agents, new pyrazoline derivatives 2a-s were synthesized and evaluated for their antidepressant-like activity by tail suspension test (TST) and modified forced swimming test (MFST). The effects of the compounds on spontaneous locomotor activity were also investigated using an activity cage apparatus. Among these derivatives, compounds 2b, 2d, 2f, 2o, and 2r decreased both horizontal and vertical activity number of the mice. On the other hand, compounds 2a, 2h, 2j, 2k, 2l, 2m, and 2n, which did not induce any significant change in the locomotor activity, significantly shortened the immobility time of mice in TST and MFST, representing the presence of the antidepressant-like effect. Additionally, the same compounds increased the swimming time of mice in MFST without any change in climbing duration, similar to the reference drug fluoxetine (10 mg/kg). In the light of previous papers examining the effects of pyrazolines on central nervous system, this study, once more, pointed out remarkable antidepressant activity potential of pyrazoline derivatives.
引用
收藏
页码:2668 / 2684
页数:17
相关论文
共 50 条
  • [1] Synthesis of Some New Chalcone and 4,5-Dihydro-1H-Pyrazole Derivatives as Potential Antimicrobial Agents
    Ibrahim, Mohammad M.
    Al-Refai, Mahmoud
    Abu-El-Halawa, Rajab
    Tashtoush, Hasan
    Alsohaili, Sohail
    Masad, Mohanad
    JORDAN JOURNAL OF CHEMISTRY, 2012, 7 (02) : 115 - 123
  • [2] Synthesis of isoxazole derivatives of 4,5-dihydro-1H-pyrazole
    A. A. Golovanov
    I. S. Odin
    A. V. Vologzhanina
    E. D. Voronova
    O. S. Anoshina
    V. V. Bekin
    Russian Journal of Organic Chemistry, 2017, 53 : 1664 - 1668
  • [3] Synthesis of Isoxazole Derivatives of 4,5-Dihydro-1H-pyrazole
    Golovanov, A. A.
    Odin, I. S.
    Vologzhanina, A. V.
    Voronova, E. D.
    Anoshina, O. S.
    Bekin, V. V.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (11) : 1664 - 1668
  • [4] Complexes of derivatives of 4,5-dihydro-1H-pyrazole as potential pesticides
    Singh, N
    Sangwan, NK
    Dhindsa, KS
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2001, 78 (03) : 119 - 122
  • [5] 3-Methyl-1,5-diphenyl-4,5-dihydro-1H-pyrazole
    Manjula, M.
    Jayaroopa, P.
    Manjunath, B. C.
    Kumar, K. Ajay
    Lokanath, N. K.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O602 - +
  • [6] NEW 4,5-DIHYDRO-1H-PYRAZOLE DERIVATIVES AS POTENTIAL NITRIC OXIDE SYNTHASE INHIBITORS
    Encarnacion Camacho, M.
    Dora Carrion, M.
    Lopez-Cara, Luisa C.
    Garcia, Esther
    Chayah, Mariem
    Entrena, Antonio
    Gallo, Miguel A.
    Espinosa, Antonio
    Lopez, Ana
    Escamez, Germaine
    Acuna-Castroviejo, Dario
    DRUGS OF THE FUTURE, 2009, 34 : 62 - 62
  • [7] 1-Acetyl-3-[4-(methylsulfanyl)phenyl]-5-(4-nitrophenyl)-4,5-dihydro-1H-pyrazole
    Thiruvalluvar, A.
    Subramanyam, M.
    Butcher, R. J.
    Mahalinga, M.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O4770 - U5617
  • [8] Ultrasonic Preparation and Reactivity of 4,5-dihydro-1H-pyrazole Derivatives
    Guesmi, Ahlem
    Ben Hamadi, Naoufel
    LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (06) : 429 - 433
  • [9] Synthesis of 4,5-dihydro-1H-pyrazole derivatives based on 3-acetyl-5-nitropyridines
    Stalinskaya, Alena L.
    Weber, Daria F.
    Seilkhanov, Tulegen M.
    Kulakov, Ivan V.
    MONATSHEFTE FUR CHEMIE, 2021, 152 (03): : 337 - 343
  • [10] Synthesis of 4,5-dihydro-1H-pyrazole derivatives based on 3-acetyl-5-nitropyridines
    Alena L. Stalinskaya
    Daria F. Weber
    Tulegen M. Seilkhanov
    Ivan V. Kulakov
    Monatshefte für Chemie - Chemical Monthly, 2021, 152 : 337 - 343