Synthesis and Pharmacological Activity of a New Series of 1-(1H-Indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol Analogs

被引:6
|
作者
Bednarski, Marek [1 ]
Otto, Monika [1 ]
Dudek, Magdalena [1 ]
Kolaczkowski, Marcin [2 ]
Bucki, Adam [2 ]
Siwek, Agata [3 ]
Groszek, Grazyna [4 ]
Maziarz, Elzbieta [5 ]
Wilk, Piotr [6 ]
Sapa, Jacek [1 ]
机构
[1] Jagiellonian Univ, Coll Med, Dept Pharmacol Screening, Fac Pharm, PL-30688 Krakow, Poland
[2] Jagiellonian Univ, Coll Med, Dept Pharmaceut Chem, Fac Pharm, PL-30688 Krakow, Poland
[3] Jagiellonian Univ, Coll Med, Dept Pharmacobiol, Fac Pharm, PL-30688 Krakow, Poland
[4] Rzeszow Univ Technol, Fac Chem, Rzeszow, Poland
[5] Inst Organ Chem, Warsaw, Poland
[6] M Nencki Inst Expt Biol, PL-02093 Warsaw, Poland
关键词
alpha(1)-; alpha(2)-; beta(1)-Adrenoreceptor antagonists; Cardiovascular activity; Enantiomers; Synthesis; PSYCHOLOGICAL SYMPTOMS; CARVEDILOL BLOCKS; BETA-BLOCKERS; DERIVATIVES; RECEPTOR; BUCINDOLOL; CURRENTS; PROTEIN;
D O I
10.1002/ardp.201500234
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
beta-Adrenergic receptor antagonists are important therapeutics for the treatment of cardiovascular disorders. In the group of beta-blockers, much attention is being paid to the third-generation drugs that possess important ancillary properties besides inhibiting beta-adrenoceptors. Vasodilating activity of these drugs is produced through different mechanisms, such as nitric oxide (NO) release, beta(2)-agonistic action, alpha(1)-blockade, antioxidant action, and Ca2+ entry blockade. Here, a study on evaluation of the cardiovascular activity of five new compounds is presented. Compound 3a is a methyl and four of the tested compounds (3b-e) are dimethoxy derivatives of 1-(1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol. The obtained results confirmed that the methyl and dimethoxy derivatives of 1-(1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol and their enantiomers possess alpha(1)- and beta(1)-adrenolytic activities and that the antiarrhythmic and hypotensive effects of the tested compounds are related to their adrenolytic properties.
引用
收藏
页码:211 / 223
页数:13
相关论文
共 50 条
  • [21] (2RS)-2-(2,4-Difluorophenyl)-1-[(4-iodobenzyl)(methyl)amino]-3-(1H-1,2,4-triazol-1-yl) propan-2-ol
    Xiong, Hui-Ping
    Gao, Shou-Hong
    Li, Chun-Tong
    Wu, Zhi-Jun
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : 02447 - +
  • [22] CRYSTAL AND MOLECULAR-STRUCTURES OF 1-(2-ETHYLOXYCARBONYLO PROPAN-2-YLAMINO)-3-(1-NAPTHYLOXY) PROPAN-2-OL-HYDROCHLORIDE (1) (C19H26NO4CL) AND 1-(2-ISOPROPYLOXYCARBONYLO-PROPAN-2-YLAMINO)-3-(1-NAPTHYLOXY) PROPAN-2-OL HYDROCHLORIDE (2) (C20H28NO4CL)
    BUJACZ, GD
    WIECZOREK, MW
    GALAS, E
    ZJAWIONY, J
    WOJCIECHOWSKA, A
    JOURNAL OF CRYSTALLOGRAPHIC AND SPECTROSCOPIC RESEARCH, 1991, 21 (03): : 341 - 352
  • [23] Polymorphism of pindolol, 1-(1H-indol-4-yloxyl)-3-isopropylamino-propan-2-ol
    Nunes, SCC
    Eusébio, ME
    Leitao, MLP
    Redinha, JS
    INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2004, 285 (1-2) : 13 - 21
  • [24] Crystal structure of 1-[2-(2,6-dichloropheny1)-4,5-dipheny1-1H-imidazol-1-yl]propan-2-ol
    Akkurt, Mehmet
    Jasinski, Jerry P.
    Mohamed, Shaaban K.
    Marzouk, Adel A.
    Albayati, Mustafa R.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O299 - U355
  • [25] (S,S,Rp)-(+)-2-{1-[1-(2-diphenylphosphinoferrocenyl)ethyl]pyrrolidin-2-yl}-propan-2-ol
    Liu, Jin-Ting
    Mao, Yan-Jun
    Xi, Ri-Muo
    Dong, Wen-Liang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : M2499 - U605
  • [26] 2-amino-2-oxazolines, part 9:: Synthesis and pharmacological evaluation of N-phenyl-N′-[1-[3-(1-aryl-4-piperazinyl)propan-2-ol]]ureas
    Bosc, JJ
    Jarry, C
    ARCHIV DER PHARMAZIE, 1998, 331 (09) : 291 - 293
  • [27] Molecular Structure and Supramolecular Architecture of Brivanib: (R)-1-(4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-5-methylpyrrolo[2,1-f] [1,2,4]triazin-6-yloxy)propan-2-ol
    Jie Cai
    Ruirui Zhang
    Crystallography Reports, 2022, 67 : 1183 - 1186
  • [28] Synthesis and positive inotropic evaluation of 1-(benzylamino)-3-(4,5-di-hydro[1,2,4]trizaolo[4,3-a]quinolin-7-yloxy)propan-2-ol derivatives
    Ting Ting Li~a Ling Zhang~b Zhe Shan Quan~a Hai Bo Zhu~(b
    Chinese Chemical Letters, 2009, 20 (02) : 175 - 177
  • [29] Molecular Structure and Supramolecular Architecture of Brivanib: (R)-1-(4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-5-methylpyrrolo[2,1-f] [1,2,4]triazin-6-yloxy)propan-2-ol
    Cai, Jie
    Zhang, Ruirui
    CRYSTALLOGRAPHY REPORTS, 2022, 67 (07) : 1183 - 1186
  • [30] Synthesis and positive inotropic evaluation of 1-(benzylamino)-3-(4,5-di-hydro[1,2,4]trizaolo[4,3-a]quinolin-7-yloxy)propan-2-ol derivatives
    Li, Ting Ting
    Zhang, Ling
    Quan, Zhe Shan
    Zhu, Hai Bo
    Piao, Hu Ri
    CHINESE CHEMICAL LETTERS, 2009, 20 (02) : 175 - 177