methyl 3-(2-(acetylthio)ethoxy)-4-iodobenzoate | 1420043-17-9

• 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: methyl 3-(2-(acetylthio)ethoxy)-4-iodobenzoate
• 英文别名: Methyl 3-(2-acetylsulfanylethoxy)-4-iodobenzoate
• CAS: 1420043-17-9
• 化学式: C₁₂H₁₃IO₄S
• 分子量: 380.203
• InChiKey: UIXBHUKDVOONEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-(acetylthio)ethoxy)-4-iodobenzoate 在 吡啶 、 甲醇 、 2,2'-联吡啶 、 水 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 nickel dichloride 、 lithium hydroxide 、 锌 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (2S,4R)-4-(difluoromethoxy)-1-[2-(2,3-dihydro-1,4-benzoxathiine-7-carbonylamino)acetyl]-N-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  PHARMACEUTICAL COMPOUNDS FOR THE TREATMENT OF COMPLEMENT MEDIATED DISORDERS

  摘要：

  This disclosure provides compounds, compositions, and methods to treat medical disorders, such as complement-mediated disorders, including complement C1s-mediated disorders.

  公开号：

  WO2024044098A2
• 作为产物：
  描述：

  3-羟基-4-碘苯甲酸甲酯 在 potassium carbonate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.0h， 生成 methyl 3-(2-(acetylthio)ethoxy)-4-iodobenzoate
  参考文献：
  名称：

  Nickel-Mediated Inter- and Intramolecular C–S Coupling of Thiols and Thioacetates with Aryl Iodides at Room Temperature

  摘要：

  A Ni(0)-catalyzed intermolecular cross-coupling of various functionalized thiols and aryl Iodides has been developed and successfully extended to less explored intramolecular versions, where thioacetates could also be utilized as the strategic surrogate. Air-stable precatalysts, very mild conditions, and an easy protocol allow rapid access to medicinally useful aryl thioethers, as demonstrated in the facile synthesis of (+/-)-chuangxinmycin as a key step.

  DOI：

  10.1021/ol303366u

文献信息

• [EN] OXO-TETRAHYDRO-ISOQUINOLINE CARBOXYLIC ACIDS AS STING INHIBITORS<br/>[FR] ACIDES OXO-TÉTRAHYDRO-ISOQUINOLINE CARBOXYLIQUES EN TANT QU'INHIBITEURS DE LA PROTÉINE STING
  申请人：MERCK SHARP & DOHME

  公开号：WO2019182886A1

  公开（公告）日：2019-09-26

  The instant invention provides compounds of formula I which are STING inhibitors, and as such are useful for the treatment of STING-mediated diseases such as inflammation, asthma, COPD and cancer.

  本发明提供了一种式I的化合物，这些化合物是STING抑制剂，因此可用于治疗STING介导的疾病，如炎症、哮喘、慢性阻塞性肺病（COPD）和癌症。
• Oxo-tetrahydro-isoquinoline carboxylic acids as STING inhibitors
  申请人：Merck Sharp & Dohme Corp.

  公开号：US11311528B2

  公开（公告）日：2022-04-26

  The instant invention provides compounds of formula I which are STING inhibitors, and as such are useful for the treatment of STING-mediated diseases such as inflammation, asthma, COPD and cancer.

  本发明提供的式 I 化合物是 STING 抑制剂，因此可用于治疗 STING 介导的疾病，如炎症、哮喘、慢性阻塞性肺病和癌症。
• Discovery of a Novel cGAMP Competitive Ligand of the Inactive Form of STING
  作者：Tony Siu、Michael D. Altman、Gretchen A. Baltus、Matthew Childers、J. Michael Ellis、Hakan Gunaydin、Harold Hatch、Thu Ho、James Jewell、Brian M. Lacey、Charles A. Lesburg、Bo-Sheng Pan、Berengere Sauvagnat、Gottfried K. Schroeder、Serena Xu

  DOI：10.1021/acsmedchemlett.8b00466

  日期：2019.1.10

  Drugging large protein pockets is a challenge due to the need for higher molecular weight ligands, which generally possess undesirable physicochemical properties. In this communication, we highlight a strategy leveraging small molecule active site dimers to inhibit the large symmetric binding pocket in the STING protein. By taking advantage of the 2:1 binding stoichiometry, maximal buried interaction with STING protein can be achieved while maintaining the ligand physicochemical properties necessary for oral exposure. This mode of binding requires unique considerations for potency optimization including simultaneous optimization of protein ligand as well as ligand ligand interactions. Successful implementation of this strategy led to the identification of 18, which exhibits good oral exposure, slow binding kinetics, and functional inhibition of STING-mediated cytokine release.
• OXO-TETRAHYDRO-ISOQUINOLINE CARBOXYLIC ACIDS AS STING INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP3768266A1

  公开（公告）日：2021-01-27