期刊文献+
任意字段
题名或关键词
题名
关键词
文摘
作者
第一作者
机构
刊名
分类号
参考文献
作者简介
基金资助
栏目信息

Synthesis, Crystal Structure and Antidepressant Activity of 5-[4-(Benzyloxy)phenyl]-9-(n-propyl)-4,6-dioxa-1-azabicyclo[3.3.1]nonane Hydrochloride 0.5Hydrate 被引量：1

Synthesis, Crystal Structure and Antidepressant Activity of 5-[4-(Benzyloxy)phenyl]-9-(n-propyl)-4,6-dioxa-1-azabicyclo[3.3.1]nonane Hydrochloride 0.5Hydrate
在线阅读 下载PDF
导出
摘要 The title compound 2（C22H28N＋O3）·H2O·2Cl-was synthesized by the reaction of 2-bromo-1-[4-（benzyloxy）phenyl]-1-pentone with 2,2＇-azanediyldiethanol. The crystal determined by X-ray diffraction analysis belongs to the monoclinic system, space group Pc with a = 18.312（3）, b = 14.838（3）, c = 7.6227（14） , β = 97.981（4）°, Z = 2, Mr = 797.82, V = 2051.1（6） 3, Dc = 1.292 g/cm3, S = 0.956, μ = 0.21 mm-1, F（000） = 852, the final R = 0.0625 and wR = 0.1428 for 5683 observed reflections （Ⅰ 〉 2σ（Ⅰ））. Flack parameter is 0.10（9）. The title compound is composed by four non-coplanar ring systems, two benzenes and two morpholines. One morpholine ring （C（3）-C（4）-N（1）-C（1）-C（2）-O（1）） forms a chair conformation, while the other （C（4）-C（3）-O（2）-C（6）-C（5）-N（1）） assumes a boat conformation. X-ray crystal structure displays extensive N-H…Cl and O-H…Cl intermolecular hydrogen bonds. The preliminary antidepressant activity test indicates that the inhibition ratio of SERT （5-HT Transporter） was 35.9% at the dosage of 10.0 mg/L. The title compound 2（C22H28N＋O3）·H2O·2Cl-was synthesized by the reaction of 2-bromo-1-[4-（benzyloxy）phenyl]-1-pentone with 2,2＇-azanediyldiethanol. The crystal determined by X-ray diffraction analysis belongs to the monoclinic system, space group Pc with a = 18.312（3）, b = 14.838（3）, c = 7.6227（14） , β = 97.981（4）°, Z = 2, Mr = 797.82, V = 2051.1（6） 3, Dc = 1.292 g/cm3, S = 0.956, μ = 0.21 mm-1, F（000） = 852, the final R = 0.0625 and wR = 0.1428 for 5683 observed reflections （Ⅰ 〉 2σ（Ⅰ））. Flack parameter is 0.10（9）. The title compound is composed by four non-coplanar ring systems, two benzenes and two morpholines. One morpholine ring （C（3）-C（4）-N（1）-C（1）-C（2）-O（1）） forms a chair conformation, while the other （C（4）-C（3）-O（2）-C（6）-C（5）-N（1）） assumes a boat conformation. X-ray crystal structure displays extensive N-H…Cl and O-H…Cl intermolecular hydrogen bonds. The preliminary antidepressant activity test indicates that the inhibition ratio of SERT （5-HT Transporter） was 35.9% at the dosage of 10.0 mg/L.
作者 付二霞 曹高 石磊 胡艾希
机构地区 College of Chemistry and Chemical Engineering School of Chemistry and Chemical Engineering
出处 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 2013年第5期709-713,共5页 结构化学（英文）
基金 Project supported by the National Technology R&D Program (No. 2011 BAE06B01)
关键词 5-[4-（benzyloxy）phenyl]-9-propyl-4 6-dioxa-l-azabicyclo [3.3.1] nonanehydrochloride SYNTHESIS crystal structure antidepressant activity 5-[4-（benzyloxy）phenyl]-9-propyl-4,6-dioxa-l-azabicyclo [3.3.1] nonanehydrochloride, synthesis, crystal structure, antidepressant activity
分类号 O621.3 [理学—有机化学]
  • 相关文献

参考文献17

  • 1Ayral-Kaloustian, S.; Curran, K. J.; Kaplan, J. A.; Richard, D. J.; Verheijen, J. C.; Zask, A Thienopyrimidine and pyrazolopyrimidine compounds and their use as mtor kinase and PI3 kinase inhibitors. US 0098086 2009.
  • 2EIShaaer, H. M.; AbdelAziz, S. A; Allimony, H. A.; Ali, U. F.; AbdelRahman, R. M. Synthesis and antimicrobial activities of some new 2-substituted benzoxazolelbenzothiazole derivatives. Pharmazie 1997, 52, 585-589.
  • 3Renslo, A. R.; Gao, H. W.; Jaishankar, P.; Venkatachalam, R.; Gomez, M.; Blais, J.; Huband, M.; Prasad, J.; Gordeev, M. F. Conformational constraint in oxazolidinone antibacterials. Part 2: Synthesis and structure-activity studies of oxa-, aza-, and thiabicyclo[3.1.0]hexylphenyl oxazolidinones. Bioorg. Med. Chem. Lett. 2006, 16, 1126-1129.
  • 4Zheng, X.; Hudyma, T. W.; Martin, S. W.; Bergstrom, C.; Ding, M.; He, F.; Romine, J.; Poss, M. A.; Kadow, J. F.; Chang, C. H.; Wan, J.; Witmer, M. R.; Morin, P.; Camac, D. M.; Sheriff, S.; Beno, B. R.; Rigat, K. J.; Wang, Y. K.; Fridell, R.; Lemm, J.; Qiu, D.; Liu, M.; Voss, S.; Pelosi, J.; Roberts, S. B.; Gao, M.; Knipe, J.; Gentles, R. G. Syntheses and initial evaluation of a series of indolo-fused heterocyclic inhibitors of the polymerase enzyme (NS5B) of the hepatitis C virus. Bioorg. Med. Chem. Lett. 2011,21,2925-2929.
  • 5Trabocchi, A; Mancini, F.; Menchi, G.; Guarna, A. A solid-phase approach towards the development of 3-aza-6,8-dioxabicyclo[3.2.I]octane scaffolds. Mol. Divers. 2003, 6, 245-250.
  • 6Ciofi, J.; Morvillo, M.; Sladojevich, F.; Guama, A.; Trabocchi, A Skeletal diversity by sequential one-pot and stepwise routes using morpholine ester scaffolds. Tetrahedron Lett. 2010,51,6282-6285.
  • 7Trabocchi, A; Menchi, G.; Guama, F.; Machetti, F.; Scarpi, D.; Guama, A. Design, synthesis, and applications of 3-aza-6,8-dioxabicyclo[3.2.I] octane-based scaffolds for peptidomimetic chemistry. Synlett. 2006,3,331-353.
  • 8Pye, P. J.; Rossen, K.; Weissman, S. A.; Maliakal, A.; Reamer, R. A.; BaH: R.; Tsou, N. N.; Volante, R. P.; Reider, P. J. Crystallization-induced diastereoselection: asymmetric synthesis of substance P inhibitors. Chem. Eur. J. 2002, 8,1372-1376.
  • 9Takashi, K.; Toshihiko, N.; Shigeto, N.; Yuuki, K.; Yasunobu, K.; Takaharu, N.; lsao, S.; Yoshimasa, M.; Seiichiro, N.; Kyosuke, K.; Kanernasa, K.; Hiroshi, Y. 3-Propeny1cephem derivative, preparation thereof, chemical intermediates therein, pharmaceutical composition and use. EU 02640911987.
  • 10Mikami, K.; Ohmura, H.; Yamanaka, M. (2,5)-Ene cyclization catalyzed by mesoporous solid acids: isotope labeling study and ab initio calculation for continuum from concerted to stepwise ene mechanism. J. Org. Chem. 2003,68,1081-1088.

同被引文献2

Chinese Journal of Structural Chemistry
2013年 第5期

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部