乙基[4-(乙硫基)苯基](氧代)乙酸酯 | 300355-73-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙基[4-(乙硫基)苯基](氧代)乙酸酯
• 英文名称: ethyl 2-(4-(ethylthio)phenyl)-2-oxoacetate
• 英文别名: Ethyl 4-(ethylthio)benzoylformate；ethyl 2-(4-ethylsulfanylphenyl)-2-oxoacetate
• CAS: 300355-73-1
• 化学式: C₁₂H₁₄O₃S
• 分子量: 238.307
• InChiKey: HTHJFEBXJXKUHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  乙基[4-(乙硫基)苯基](氧代)乙酸酯 在 盐酸 、 palladium 10% on activated carbon 、 盐酸羟胺 、 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 间氯过氧苯甲酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 44.0h， 生成 2-amino-2-[4-(ethylsulfonyl)phenyl]-N-[4-(2-{[4-(trifluoromethoxy)benzyl]oxy}pyridin-3-yl)thiophen-2-yl]acetamide
  参考文献：
  名称：

  Potent and Orally Bioavailable Inverse Agonists of RORγt Resulting from Structure-Based Design

  摘要：

  Retinoic acid receptor related orphan receptor gamma t (ROR gamma t), has been identified as the master regulator of T(H)17-cell function and development, making it an attractive target for the treatment of autoimmune diseases by a small-molecule approach. Herein, we describe our investigations on a series of 4-aryl-thienyl acetamides, which were guided by insights from X-ray cocrystal structures. Efforts in targeting the cofactor-recruitment site from the 4-aryl group on the thiophene led to a series of potent binders with nanomolar activity in a primary human-T(H)17-cell assay. The observation of a DMSO molecule binding in a subpocket outside the LBD inspired the introduction of an acetamide into the benzylic position of these compounds. Hereby, a hydrogen-bond interaction of the introduced acetamide oxygen with the backbone amide of Glu379 was established. This greatly enhanced the cellular activity of previously weakly cell-active compounds. The best compounds combined potent inhibition of IL-17 release with favorable PK in rodents, with compound 32 representing a promising starting point for future investigations.

  DOI：

  10.1021/acs.jmedchem.8b00783
• 作为产物：
  描述：

  苯乙硫醚 、 草酰氯单乙酯 在 三氯化铝 作用下， 以 氯仿 为溶剂， 以55%的产率得到乙基[4-(乙硫基)苯基](氧代)乙酸酯
  参考文献：
  名称：

  Heteroaromatic glucokinase activators

  摘要：

  2,3-二取代N-杂环丙酰胺，其中3位取代为取代苯基，2位取代为甲基环烷基环，这些丙酰胺是葡萄糖激酶激活剂，可增加胰岛素分泌，用于治疗2型糖尿病。

  公开号：

  US06610846B1

文献信息

• Dihydropyrrolopyridine inhibitors of ROR-gamma
  申请人：Vitae Pharmaceuticals, Inc.

  公开号：US09481674B1

  公开（公告）日：2016-11-01

  Provided are novel compounds of Formula (I): pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful in the treatment of diseases and disorders mediated by RORγ. Also provided are pharmaceutical compositions comprising the novel compounds of Formula (I) and methods for their use in treating one or more inflammatory, metabolic, autoimmune and other diseases or disorders.

  提供了式(I)的新化合物：其药用盐，以及其药物组合物，可用于治疗由RORγ介导的疾病和紊乱。还提供了包含式(I)的新化合物的药物组合物，以及在治疗一种或多种炎症性、代谢性、自身免疫和其他疾病或紊乱中使用它们的方法。
• [EN] DIHYDROPYRROLOPYRIDINE INHIBITORS OF ROR-GAMMA<br/>[FR] INHIBITEURS DE ROR-GAMMA À BASE DE DIHYDROPYRROLOPYRIDINE
  申请人：VITAE PHARMACEUTICALS INC

  公开号：WO2016061160A1

  公开（公告）日：2016-04-21

  Provided are novel compounds of Formula (I): pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful in the treatment of diseases and disorders mediated by RORy. Also provided are pharmaceutical compositions comprising the novel compounds of Formula (I) and methods for their use in treating one or more inflammatory, metabolic, autoimmune and other diseases or disorders.

  提供了式（I）的新化合物：其药用盐以及药物组合物，可用于治疗由RORγ介导的疾病和紊乱。还提供了包含式（I）的新化合物的药物组合物，以及它们在治疗一种或多种炎症性、代谢性、自身免疫和其他疾病或紊乱中的使用方法。
• Direct Synthesis of <i>N</i>-Alkyl Arylglycines by Organocatalytic Asymmetric Transfer Hydrogenation of <i>N</i>-Alkyl Aryl Imino Esters
  作者：Javier Mazuela、Thomas Antonsson、Magnus J. Johansson、Laurent Knerr、Stephen P. Marsden

  DOI：10.1021/acs.orglett.7b02627

  日期：2017.10.20

  The organocatalytic asymmetric transfer hydrogenation of N-alkyl aryl imino esters for the direct synthesis of N-alkylated arylglycinate esters is reported. High yields and enantiomeric ratios were obtained, and tolerance to a diverse set of functional groups facilitated the preparation of more complex molecules as well as intermediates for active pharmaceuticals. A simple recycling protocol was developed

  报道了用于直接合成N-烷基化的芳基甘氨酸酯的有机催化的N-烷基芳基亚氨基亚氨基酯的不对称转移氢化。获得了高产率和对映体比率，并且对各种官能团的耐受性促进了更复杂的分子以及活性药物中间体的制备。针对布朗斯台德酸催化剂开发了一种简单的回收方案，该方案可以通过五个循环重复使用，而不会损失活性或选择性。
• Urea derivatives
  申请人：Hoffman-La Roche Inc.

  公开号：US06528543B1

  公开（公告）日：2003-03-04

  Glucokinase activating compounds of the formula wherein R1 and R2 are independently hydrogen, halo, amino, nitro, cyano, sulfonamido, lower alkyl, perfluoro-lower alkyl, lower alkyl thio, perfluoro-lower alkyl thio, lower alkyl sulfonyl, or perfluoro-lower alkyl sulfonyl; R3 is cycloalkyl having from 3 to 7 carbon atoms or lower alkyl having from 2 to 4 carbon atoms; R4 is hydrogen, lower alkyl, lower alkenyl, hydroxy lower alkyl, halo lower alkyl, R5 and R6 are hydrogen or lower alkyl; and n is 0, 1, 2, 3 or 4; or a pharmaceutically acceptable salt thereof

  该公式中的激活葡萄糖激酶化合物，其中R1和R2独立地为氢、卤素、氨基、硝基、氰基、磺酰胺基、低碳基、全氟低碳基、低碳硫基、全氟低碳硫基、低碳基磺酰基或全氟低碳基磺酰基；R3为具有3至7个碳原子的环烷基或具有2至4个碳原子的低碳基；R4为氢、低碳基、低碳烯基、羟基低碳基或卤素低碳基；R5和R6为氢或低碳基；n为0、1、2、3或4；或其药学上可接受的盐。
• CYCLOPENTYLACRYLIC ACID AMIDE DERIVATIVE
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：EP2275414A1

  公开（公告）日：2011-01-19

  A compound having a hypoglycemic effect is provided. The compound and a pharmaceutically acceptable salt thereof are useful for the treatment or prevention of diabetes, obesity, and the like. The compound is represented by the general formula (1): (wherein R1 and R2 are each independently a hydrogen atom, a halogen atom, an amino group, a hydroxyl group, a hydroxyamino group, a nitro group, a cyano group, a sulfamoyl group, a C1 to C6 alkyl group, a C1 to C6 alkoxy group, a C1 to C6 alkylsulfonyl group, a C1 to C6 alkylsulfinyl group, a C1 to C6 alkylsulfonyl group, or a C1 to C6 alkoxy-C1 to C6 alkylsulfonyl group, and A is a substituted or unsubstituted heteroaryl group).

  本研究提供了一种具有降血糖作用的化合物。该化合物及其药学上可接受的盐可用于治疗或预防糖尿病、肥胖症等。该化合物由通式（1）表示： (其中 R1 和 R2 各自独立地为氢原子、卤素原子、氨基、羟基、羟基氨基、硝基、氰基、氨基磺酰基、C1 至 C6 烷基、C1 至 C6 烷氧基、C1 至 C6 烷烃基、C1 至 C6 烷烃基、C1 至 C6 烷烃基、C1 至 C6 烷氧基、C1 至 C6 烷烃基、C1 至 C6 烷烃基、C1 至 C6 烷烃基、C1 至 C6 烷氧基C1-C6烷基磺酰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或 C1-C6烷氧基-C1-C6烷基磺酰基，且 A 是取代或未取代的杂芳基）。