(2-amino-5-chlorophenyl)(2,6-dimethoxyphenyl)methanone | 152911-39-2

• 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: (2-amino-5-chlorophenyl)(2,6-dimethoxyphenyl)methanone
• 英文别名: (2-amino-5-chlorophenyl)-(2,6-dimethoxyphenyl)methanone
• CAS: 152911-39-2
• 化学式: C₁₅H₁₄ClNO₃
• 分子量: 291.734
• InChiKey: KRVVFKIDHZSSEA-UHFFFAOYSA-N

物化性质

• 沸点：
  503.8±50.0 °C(predicted)
• 密度：
  1.269±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  61.55
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2-amino-5-chlorophenyl)(2,6-dimethoxyphenyl)methanone 在 ammonium acetate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 104.0h， 生成 N-{[6-chloro-4-(2,6-dimethoxyphenyl)quinazolin-2-yl]carbonyl}-L-leucine
  参考文献：
  名称：

  Identification of N-{[6-chloro-4-(2,6-dimethoxyphenyl)quinazolin-2-yl]carbonyl}-l-leucine (NTRC-808), a novel nonpeptide chemotype selective for the neurotensin receptor type 2

  摘要：

  Compounds acting via the GPCR neurotensin receptor type 2 (NTS2) display analgesic effects in relevant animal models. Using a pharmacophore model based on known NT receptor nonpeptide compounds, we screened commercial databases to identify compounds that might possess activity at NTS2 receptor sites. Modification of our screening hit to include structural features known to be recognized by NTS1 and NTS2, led to the identification of the novel NTS2 selective nonpeptide, N-{[6-chloro-4-(2,6-dimethoxyphenyl) quinazolin-2-yl] carbonyl}-L-leucine (9). This compound is a potent partial agonist in the FLIPR assay with a profile of activity similar to that of the reference NTS2 analgesic nonpeptide levocabastine (5). (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.11.047
• 作为产物：
  描述：

  2-氨基-5-氯苯甲酸 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 (2-amino-5-chlorophenyl)(2,6-dimethoxyphenyl)methanone
  参考文献：
  名称：

  Identification of N-{[6-chloro-4-(2,6-dimethoxyphenyl)quinazolin-2-yl]carbonyl}-l-leucine (NTRC-808), a novel nonpeptide chemotype selective for the neurotensin receptor type 2

  摘要：

  Compounds acting via the GPCR neurotensin receptor type 2 (NTS2) display analgesic effects in relevant animal models. Using a pharmacophore model based on known NT receptor nonpeptide compounds, we screened commercial databases to identify compounds that might possess activity at NTS2 receptor sites. Modification of our screening hit to include structural features known to be recognized by NTS1 and NTS2, led to the identification of the novel NTS2 selective nonpeptide, N-{[6-chloro-4-(2,6-dimethoxyphenyl) quinazolin-2-yl] carbonyl}-L-leucine (9). This compound is a potent partial agonist in the FLIPR assay with a profile of activity similar to that of the reference NTS2 analgesic nonpeptide levocabastine (5). (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.11.047

文献信息

• Novel 4,1-benzoxazepine derivatives with potent squalene synthase inhibitory activities
  作者：Takashi Miki、Masakuni Kori、Hiroshi Mabuchi、Hiroshi Banno、Ryu-ichi Tozawa、Masahira Nakamura、Shigekazu Itokawa、Yasuo Sugiyama、Hidefumi Yukimasa

  DOI：10.1016/s0968-0896(01)00290-5

  日期：2002.2

  inhibitory activity. Among such compounds, the 5-(2,3-dimethoxyphenyl) derivative 2t exhibited potent inhibition of cholesterol biosynthesis in HepG2 cells. As a result of optical resolution study of 2t, the absolute stereochemistry required for inhibitory activity was determined to be 3R,5S. In vivo study showed that the sodium salt of (3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4

  合成了一系列的（3,5-反式）-2-氧代-5-苯基-1,2,3,5-四氢-4,1-苯并x氮平衍生物，并评价了其对角鲨烯合酶的抑制作用和对胆固醇生物合成的抑制作用。通过修饰先导化合物1a和1b的取代基，发现在1位带有异丁基和新戊基，在7位具有氯原子和在氯原子上具有4，1-苯并氮杂氮杂-3-乙酸衍生物。在5-苯环的2'-位上的甲氧基具有强力的角鲨烯合酶抑制活性。在这些化合物中，5-（2,3-二甲氧基苯基）衍生物2t在HepG2细胞中显示出有效的胆固醇生物合成抑制作用。作为2t光学拆分研究的结果，抑制活性所需的绝对立体化学被确定为3R，5S。