{4-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethylsulfanyl]-2,6-difluorophenoxy}acetic acid ethyl ester | 141286-84-2

• 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-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethylsulfanyl]-2,6-difluorophenoxy}acetic acid ethyl ester
• 英文别名: {4-[2-(1,3-dioxo-1,3-dihydroisoindole-2-yl)ethylsulfanil]-2,6-difluorophenoxy}ethylacetic acid ester；ethyl 2,6-difluoro-4-<2-(phthalimid-2-yl)ethylthio>phenoxyacetate；Ethyl 2-[4-[2-(1,3-dioxoisoindol-2-yl)ethylsulfanyl]-2,6-difluorophenoxy]acetate
• CAS: 141286-84-2
• 化学式: C₂₀H₁₇F₂NO₅S
• 分子量: 421.421
• InChiKey: TUKZWSDOTQXLIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {4-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethylsulfanyl]-2,6-difluorophenoxy}acetic acid ethyl ester 在 氨 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 2-{2,6-difluoro-4-[2-(4-methylbenzenesulfonylamino)ethylsulfanyl]phenoxy}acetamide
  参考文献：
  名称：

  JP6241974

  摘要：

  公开号：
• 作为产物：
  描述：

  2,6-二氟苯酚 在 氯磺酸 、 硫酸 、 potassium carbonate 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 {4-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethylsulfanyl]-2,6-difluorophenoxy}acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis and evaluation of novel fluorinated sulotroban-related sulfonamide derivatives as thromboxane A2 receptor antagonists

  摘要：

  A series of sulotroban-related arylsulfonamide derivatives possessing a fluorinated phenoxyacetic acid moiety was synthesized and tested for TXA(2) antagonizing ability on U-46619-induced platelet aggregation of rabbit platelet-rich plasma. Introduction of one or more fluorine atoms to the phenoxyacetic acid moiety increased this activity. The most potent compound among these compounds was 10c, which was 40-fold more potent (IC50 3.4 x 10(-7) M) than sulotroban. 10c exhibited high activity (ID50, 0.14 mg/kg) against a U-46619-induced acute thrombocytopenia model in mice when orally administrated. These findings and those of radioligand binding assays with various ligands showed 10c to be a potent and selective systemic TXA, receptor antagonist.

  DOI：

  10.1016/0223-5234(96)88250-x

文献信息

• PROPHYLACTIC AND/OR THERAPEUTIC AGENT FOR DISEASES ASSOCIATED WITH AMPA RECEPTORS
  申请人：Public University Corporation Yokohama City University

  公开号：EP3569229A1

  公开（公告）日：2019-11-20

  This prophylactic and/or therapeutic agent for diseases associated with AMPA receptors contains a compound represented by formula (I), or a pharmaceutically acceptable salt or solvate thereof. (In the formula, A and Z independently represent CO, SO or SO2; X and Y are independently S or O; R1-R4 are independently hydrogen, an alkyl group, an alkenyl group, an alkynyl group or a halo group; R5 is, independently for each occurrence, an alkyl group, an alkenyl group, an alkynyl group or a halo group; and n is an integer of 0-4).

  这种与 AMPA 受体相关疾病的预防和/或治疗剂含有由式 (I) 代表的化合物或其药学上可接受的盐或溶液。(式中，A 和 Z 独立地代表 CO、SO 或 SO2；X 和 Y 独立地为 S 或 O；R1-R4 独立地为氢、烷基、烯基、炔基或卤代基团；R5 在每次出现时独立地为烷基、烯基、炔基或卤代基团；n 为 0-4 的整数）。
• Compound that specifically binds to AMPA receptor
  申请人：Public University Corporation Yokohama City University

  公开号：US10335503B2

  公开（公告）日：2019-07-02

  The present invention provides a compound represented by formula (I), a pharmaceutically acceptable salt thereof or a solvate thereof. (In the formula, each of A and Z independently represents CO, SO or SO2; each of X and Y independently represents S or O; each of R1-R4 independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or a halogen group; each R5 independently represents an alkyl group, an alkenyl group, an alkynyl group or a halogen group; and n represents an integer of 0-4.) This compound is capable of specifically binding to an AMPA receptor, and shows extremely high brain uptake.

  本发明提供了一种由式 (I) 代表的化合物、其药学上可接受的盐或其溶液。 (式中，A和Z各自独立地代表CO、SO或SO2；X和Y各自独立地代表S或O；R1-R4各自独立地代表氢原子、烷基、烯基、炔基或卤素基；R5各自独立地代表烷基、烯基、炔基或卤素基；n代表0-4的整数)。这种化合物能够与 AMPA 受体特异性结合，并显示出极高的脑吸收率。
• EP3569229
  申请人：——

  公开号：——

  公开（公告）日：——
• NOVEL COMPOUND THAT SPECIFICALLY BINDS TO AMPA RECEPTOR
  申请人：PUBLIC UNIVERSITY CORPORATION YOKOHAMA CITY UNIVERSITY

  公开号：US20180200391A1

  公开（公告）日：2018-07-19

  The present invention provides a compound represented by formula (I), a pharmaceutically acceptable salt thereof or a solvate thereof. (In the formula, each of A and Z independently represents CO, SO or SO 2 ; each of X and Y independently represents S or O; each of R 1 -R 4 independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or a halogen group; each R 5 independently represents an alkyl group, an alkenyl group, an alkynyl group or a halogen group; and n represents an integer of 0-4.) This compound is capable of specifically binding to an AMPA receptor, and shows extremely high brain uptake.
• IMAGING METHOD OF AMPA RECEPTORS IN BRAIN OF PRIMATE ORGANISM, PROGRAM, DIAGNOSTIC AGENT, COMPANION DIAGNOSTIC AGENT, DRUG, SCREENING METHOD, INPUT TERMINAL, SERVER AND SYSTEM
  申请人：Public University Corporation Yokohama City University

  公开号：US20200384134A1

  公开（公告）日：2020-12-10

  This imaging method of AMPA receptors in the brain of primate organisms involves a step in which a substance which is administered to the primate organism and which selectively bonds to AMPA receptors in the brain of the primate organism and has a radiolabel is transported into the brain and made to bond with AMPA receptors in the brain, and, by detecting radiation emitted from the substance bonded to the AMPA receptors in the brain, data is obtained relating to the distribution and/or expression level of the AMPA receptors in the brain.