4-[2-(Propan-2-yl)phenoxy]benzoic acid | 938271-18-2

• 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: 4-[2-(Propan-2-yl)phenoxy]benzoic acid
• 英文别名: 4-(2-propan-2-ylphenoxy)benzoic acid
• CAS: 938271-18-2
• 化学式: C₁₆H₁₆O₃
• mdl: MFCD09713539
• 分子量: 256.301
• InChiKey: JGVSWKJMPWLSET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[2-(Propan-2-yl)phenoxy]benzoic acid 在 四丁基氟化铵 、 1-羟基苯并三唑 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 (4-ethyl-5-(5-(4-(2-isopropylphenoxy)phenyl)-1,2,4-oxadiazol-3-yl)thiophen-2-yl)methanol
  参考文献：
  名称：

  Discovery of CS-2100, a potent, orally active and S1P3-sparing S1P1 agonist

  摘要：

  S1P(3)-sparing S1P(1) agonists have attracted attention as a suppressant of autoimmunity with reduced side effects. Our synthetic efforts and extensive SAR studies led to the discovery of 10b named CS-2100 with the EC50 value of 4.0 nM for human S1P(1) and over 5000-fold selectivity against S1P(3). The in vivo immunosuppressive efficacy was evaluated in rats on host versus graft reaction and the ID50 value was determined at 0.407 mg/kg. The docking studies of CS-2100 with the homology model of S1P(1) and S1P(3) showed that the ethyl group on the thiophene ring of CS-2100 was sterically hindered by Phe263 in S1P(3), not in the case of Leu276 in S1P(1). This observation gives an explanation for the excellent S1P(3)-sparing characteristic of CS-2100. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.019
• 作为产物：
  描述：

  异丙苯酚 在 sodium chlorite 、 potassium dihydrogenphosphate 、 2-甲基-2-丁烯 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 4-[2-(Propan-2-yl)phenoxy]benzoic acid
  参考文献：
  名称：

  Discovery of CS-2100, a potent, orally active and S1P3-sparing S1P1 agonist

  摘要：

  S1P(3)-sparing S1P(1) agonists have attracted attention as a suppressant of autoimmunity with reduced side effects. Our synthetic efforts and extensive SAR studies led to the discovery of 10b named CS-2100 with the EC50 value of 4.0 nM for human S1P(1) and over 5000-fold selectivity against S1P(3). The in vivo immunosuppressive efficacy was evaluated in rats on host versus graft reaction and the ID50 value was determined at 0.407 mg/kg. The docking studies of CS-2100 with the homology model of S1P(1) and S1P(3) showed that the ethyl group on the thiophene ring of CS-2100 was sterically hindered by Phe263 in S1P(3), not in the case of Leu276 in S1P(1). This observation gives an explanation for the excellent S1P(3)-sparing characteristic of CS-2100. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.019

文献信息

• Discovery of CS-2100, a potent, orally active and S1P3-sparing S1P1 agonist
  作者：Tsuyoshi Nakamura、Masayoshi Asano、Yukiko Sekiguchi、Yumiko Mizuno、Kazuhiko Tamaki、Takako Kimura、Futoshi Nara、Yumi Kawase、Takaichi Shimozato、Hiromi Doi、Takashi Kagari、Wataru Tomisato、Ryotaku Inoue、Miyuki Nagasaki、Hiroshi Yuita、Keiko Oguchi-Oshima、Reina Kaneko、Nobuaki Watanabe、Yasuyuki Abe、Takahide Nishi

  DOI：10.1016/j.bmcl.2011.12.019

  日期：2012.2

  S1P(3)-sparing S1P(1) agonists have attracted attention as a suppressant of autoimmunity with reduced side effects. Our synthetic efforts and extensive SAR studies led to the discovery of 10b named CS-2100 with the EC50 value of 4.0 nM for human S1P(1) and over 5000-fold selectivity against S1P(3). The in vivo immunosuppressive efficacy was evaluated in rats on host versus graft reaction and the ID50 value was determined at 0.407 mg/kg. The docking studies of CS-2100 with the homology model of S1P(1) and S1P(3) showed that the ethyl group on the thiophene ring of CS-2100 was sterically hindered by Phe263 in S1P(3), not in the case of Leu276 in S1P(1). This observation gives an explanation for the excellent S1P(3)-sparing characteristic of CS-2100. (C) 2011 Elsevier Ltd. All rights reserved.