N-(2-aminoethyl)-2-methoxy-5-methylbenzamide | 1249480-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-aminoethyl)-2-methoxy-5-methylbenzamide
• CAS: 1249480-68-9
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: VPCGYPHEHHFORH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-aminoethyl)-2-methoxy-5-methylbenzamide 、 pentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>-undecan-8,11-dione monoethyleneacetal 以 乙醇 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Molecular hybridization of 4-azahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecane-3-ol with sigma (σ) receptor ligands modulates off-target activity and subtype selectivity

  摘要：

  A series of N-substituted 4-azahexacyclo[5.4.1.0(2,6).0(3,10).0(5,9).0(8,11)] dodecan-3-ols incorporating the respective arylalkyl subunits from several known sigma (sigma) receptor ligands were synthesized and evaluated for their affinity against sigma receptors and dopamine receptors. The hybrid trishomocubane-derived ligands (4-6) showed good selectivity for sigma(1) and sigma(2) receptors over multiple dopamine receptors. The molecular hybrid obtained from haloperidol and 4-azahexacyclo[ 5.4.1.0(2,6).0(3,10).0(5,9).0(8,11)] dodecan-3-ol (4, sigma(1) K-i = 27 nM, sigma(2) K-i = 55 nM) showed reduced affinity for D-1-D-5 dopamine receptors when compared to haloperidol itself. The compound with the greatest sigma(1) affinity in the series, benzamide 4 (sigma(1) K-i = 7.6 nM, sigma(2) K-i = 225 nM) showed a complete reversal of the subtype selectivity displayed by the highly sigma(2) selective parent benzamide, RHM-2 (3, sigma(1) K-i = 10412 nM, sigma(2) K-i = 13.3 nM). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.098
• 作为产物：
  描述：

  2-甲氧基-5-甲基苯甲酸 、 乙二胺 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以95%的产率得到N-(2-aminoethyl)-2-methoxy-5-methylbenzamide
  参考文献：
  名称：

  Molecular hybridization of 4-azahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecane-3-ol with sigma (σ) receptor ligands modulates off-target activity and subtype selectivity

  摘要：

  A series of N-substituted 4-azahexacyclo[5.4.1.0(2,6).0(3,10).0(5,9).0(8,11)] dodecan-3-ols incorporating the respective arylalkyl subunits from several known sigma (sigma) receptor ligands were synthesized and evaluated for their affinity against sigma receptors and dopamine receptors. The hybrid trishomocubane-derived ligands (4-6) showed good selectivity for sigma(1) and sigma(2) receptors over multiple dopamine receptors. The molecular hybrid obtained from haloperidol and 4-azahexacyclo[ 5.4.1.0(2,6).0(3,10).0(5,9).0(8,11)] dodecan-3-ol (4, sigma(1) K-i = 27 nM, sigma(2) K-i = 55 nM) showed reduced affinity for D-1-D-5 dopamine receptors when compared to haloperidol itself. The compound with the greatest sigma(1) affinity in the series, benzamide 4 (sigma(1) K-i = 7.6 nM, sigma(2) K-i = 225 nM) showed a complete reversal of the subtype selectivity displayed by the highly sigma(2) selective parent benzamide, RHM-2 (3, sigma(1) K-i = 10412 nM, sigma(2) K-i = 13.3 nM). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.098

文献信息

• QUINOLONE COMPOUND
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：EP3318557A2

  公开（公告）日：2018-05-09

  The present invention provides a compound represented by the formula (I) wherein X is a hydrogen atom or a fluorine atom; R is a hydrogen atom or alkyl; R1 is (1) cyclopropyl optionally substituted by 1 to 3 halogen atoms or (2) phenyl optionally substituted by 1 to 3 halogen atoms; R2 is alkyl, alkoxy, haloalkoxy, a halogen atom, cyano, etc.; and R3 is 7-oxo-7,8-dihydro-1,8-naphthyridinyl, 3-pyridyl, etc., or a salt thereof. The compound of the present invention has excellent antimicrobial activity against Clostridium difficile and is useful for the prevention or treatment of intestinal infection such as Clostridium difficile-associated diarrhea.

  本发明提供了一种由式 (I) 表示的化合物 其中 X 是氢原子或氟原子；R 是氢原子或烷基；R1 是(1)任选被 1 至 3 个卤素原子取代的环丙基或(2)任选被 1 至 3 个卤素原子取代的苯基；R2 是烷基、烷氧基、卤代烷氧基、卤素原子、氰基等；R3 是 7-氧代-7,8-二氢-1,8-萘啶基、3-吡啶基等或其盐。本发明的化合物对艰难梭菌具有优异的抗菌活性，可用于预防或治疗艰难梭菌相关性腹泻等肠道感染。
• Compounds For Use In Treatment Of Mucositis
  申请人：Scott Richard W.

  公开号：US20120295922A1

  公开（公告）日：2012-11-22

  The present invention provides methods for treating and/or preventing mucostitis with one or more compounds, or pharmaceutically acceptable salts thereof, disclosed herein, or compositions comprising the same.
• US8802683B2
  申请人：——

  公开号：US8802683B2

  公开（公告）日：2014-08-12
• Molecular hybridization of 4-azahexacyclo[5.4.1.02,6.03,10.05,9.08,11]dodecane-3-ol with sigma (σ) receptor ligands modulates off-target activity and subtype selectivity
  作者：Samuel D. Banister、Iman A. Moussa、William T. Jorgensen、Sook Wern Chua、Michael Kassiou

  DOI：10.1016/j.bmcl.2011.04.098

  日期：2011.6

  A series of N-substituted 4-azahexacyclo[5.4.1.0(2,6).0(3,10).0(5,9).0(8,11)] dodecan-3-ols incorporating the respective arylalkyl subunits from several known sigma (sigma) receptor ligands were synthesized and evaluated for their affinity against sigma receptors and dopamine receptors. The hybrid trishomocubane-derived ligands (4-6) showed good selectivity for sigma(1) and sigma(2) receptors over multiple dopamine receptors. The molecular hybrid obtained from haloperidol and 4-azahexacyclo[ 5.4.1.0(2,6).0(3,10).0(5,9).0(8,11)] dodecan-3-ol (4, sigma(1) K-i = 27 nM, sigma(2) K-i = 55 nM) showed reduced affinity for D-1-D-5 dopamine receptors when compared to haloperidol itself. The compound with the greatest sigma(1) affinity in the series, benzamide 4 (sigma(1) K-i = 7.6 nM, sigma(2) K-i = 225 nM) showed a complete reversal of the subtype selectivity displayed by the highly sigma(2) selective parent benzamide, RHM-2 (3, sigma(1) K-i = 10412 nM, sigma(2) K-i = 13.3 nM). (C) 2011 Elsevier Ltd. All rights reserved.