3-chloro-4-phenoxybenzoic acid | 74917-55-8

• 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: 3-chloro-4-phenoxybenzoic acid
• CAS: 74917-55-8
• 化学式: C₁₃H₉ClO₃
• 分子量: 248.666
• InChiKey: BHGHJIYJDMJREN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-chloro-4-phenoxybenzoic acid 在 四溴化碳 、 四丁基氟化铵 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 methyl 1-({5-[5-(3-chloro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-4-ethyl-2-thienyl}methyl)azetidine-3-carboxylate
  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：

  3-氯-4-氟苯甲醛 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 3-chloro-4-phenoxybenzoic 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

• Heterocyclic compound
  申请人：Nishi Takahide

  公开号：US20080113961A1

  公开（公告）日：2008-05-15

  A compound having immunosuppressive activity with low toxicity or a pharmacological salt thereof. The compound has a general formula (I) shown below or a pharmacologically acceptable salt thereof, or a pharmacologically acceptable prodrug thereof

  具有低毒性免疫抑制活性的化合物或其药理盐。该化合物具有下面所示的一般式（I）或其药理学上可接受的盐，或其药理学上可接受的前体。
• 2H-CHROMENE COMPOUND AND DERIVATIVE THEREOF
  申请人：Harada Hironori

  公开号：US20120178735A1

  公开（公告）日：2012-07-12

  Provided is a 2H-chromene compound or a derivative thereof which has an excellent S1P1 agonist action. The 2H-chromene compound or derivative is particularly useful for preventing and/or treating a disease induced by undesirable lymphocyte infiltration or a disease induced by abnormal proliferation or accumulation of cells.

  提供了一种2H-色烯化合物或其衍生物，具有优异的S1P1激动剂作用。该2H-色烯化合物或衍生物特别适用于预防和/或治疗由不良淋巴细胞浸润引起的疾病或由细胞异常增殖或堆积引起的疾病。
• Substituted Heteroarylalkanoic Acids
  申请人：Van Zandt Michael C.

  公开号：US20090163535A1

  公开（公告）日：2009-06-25

  Disclosed are substituted heteroarylalkanoic acids of the following formula D-A-C(O)R′, where D, A, and R′ are defined herein. These compounds are useful in the treatment of chronic complications arising from diabetes mellitus. Also disclosed are pharmaceutical compositions containing the compounds and methods of treatment employing the compounds, as well as methods for their synthesis.

  本发明揭示了下式D-A-C(O)R′的取代杂环烷基脂肪酸，其中D，A和R′在此定义。这些化合物可用于治疗由糖尿病引起的慢性并发症。此外，还揭示了含有这些化合物的药物组合物和使用这些化合物的治疗方法，以及它们的合成方法。
• Discovery of BGB-8035, a Highly Selective Covalent Inhibitor of Bruton’s Tyrosine Kinase for B-Cell Malignancies and Autoimmune Diseases
  作者：Yunhang Guo、Nan Hu、Ye Liu、Wei Zhang、Desheng Yu、Gongyin Shi、Bo Zhang、Longbo Yin、Min Wei、Xi Yuan、Lusong Luo、Fan Wang、Xiaomin Song、Lei Xin、Qiang Wei、Yong Li、Ying Guo、Shuaishuai Chen、Taichang Zhang、Shuo Zhang、Xing Zhou、Cuining Zhang、Dan Su、Junhua Liu、Zhenzhen Cheng、Jiye Zhang、Haimei Xing、Hanzi Sun、Xin Li、Yuan Zhao、Min He、Yue Wu、Yin Guo、Xuebing Sun、Alice Tian、Changyou Zhou、Steve Young、Xuesong Liu、Lai Wang、Zhiwei Wang

  DOI：10.1021/acs.jmedchem.2c01938

  日期：2023.3.23

  Bruton’s tyrosine kinase (BTK) plays an essential role in B-cell receptor (BCR)-mediated signaling as well as the downstream signaling pathway for Fc receptors (FcRs). Targeting BTK for B-cell malignancies by interfering with BCR signaling has been clinically validated by some covalent inhibitors, but suboptimal kinase selectivity may lead to some adverse effects, which also makes the clinical development

  Bruton 酪氨酸激酶 (BTK) 在 B 细胞受体 (BCR) 介导的信号转导以及 Fc 受体 (FcR) 的下游信号转导通路中起着重要作用。通过干扰 BCR 信号通路靶向 BTK 治疗 B 细胞恶性肿瘤已经通过一些共价抑制剂进行了临床验证，但不理想的激酶选择性可能会导致一些不良反应，这也使得自身免疫性疾病治疗的临床开发更具挑战性。从zanubrutinib ( BGB - 3111 )开始的构效关系(SAR)导致一系列高选择性BTK抑制剂，其中BGB - 8035位于 ATP 结合口袋中，与 ATP 具有相似的铰链结合，但对其他激酶（EGFR、Tec 等）表现出高选择性。BGB - 8035具有出色的药代动力学特征以及在肿瘤学和自身免疫性疾病模型中证明的疗效研究，已被宣布为临床前候选药物。然而，与BGB - 3111相比，BGB - 8035的毒性较低。
• Deep ultraviolet absorbent and its use in pattern formation
  申请人：WAKO PURE CHEMICAL INDUSTRIES LTD

  公开号：EP0636941A1

  公开（公告）日：1995-02-01

  A deep ultraviolet absorbent comprising at least one compound having one or more glycidyl groups in the molecule and at least one anthracene derivative, and a solvent capable of dissolving these compounds is effective for preventing reflection of deep ultraviolet light from a substrate during formation of resist pattern, resulting in forming ultra-fine patterns without causing notching and halation.

  深紫外线吸收剂包含至少一种在分子中含有一个或多个缩水甘油基团的化合物和至少一种蒽衍生物，以及一种能够溶解这些化合物的溶剂，可有效防止在形成抗蚀剂图案的过程中深紫外线从基底反射，从而形成超精细图案，且不会造成缺口和光晕。