3-溴-4-氧代庚二酸二乙酯 | 59742-68-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 3-溴-4-氧代庚二酸二乙酯
• 英文名称: bromo-3 oxo-4 pimelate d'ethyle
• 英文别名: diethyl 3-bromo-4-oxoheptanedioate；Ethyl 3-bromo-4-oxo-pimelate；Diethyl 3-bromo-4-oxoheptanedioate
• CAS: 59742-68-6
• 化学式: C₁₁H₁₇BrO₅
• 分子量: 309.157
• InChiKey: NAISJJKROKNKCI-UHFFFAOYSA-N

物化性质

• 沸点：
  363.6±27.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-溴-4-氧代庚二酸二乙酯 在 镍 盐酸 、 乙醚 、 氢气 、 sodium 作用下， 以 乙醇 为溶剂， 20.0~90.0 ℃ 、9.0 MPa 条件下， 反应 124.0h， 生成 依曲巴明
  参考文献：
  名称：

  Maillard; Delaunay; Langlois, European Journal of Medicinal Chemistry, 1984, vol. 19, # 5, p. 451 - 456

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氧代庚二酸二乙酯 在 溴 作用下， 以74%的产率得到3-溴-4-氧代庚二酸二乙酯
  参考文献：
  名称：

  4-氧-庚二酸类似物对二氢二吡啶甲酸酯合酶的不可逆抑制作用。

  摘要：

  我们报告了（2E，5E）-4-氧庚二烯二酸和（2E）-4-氧庚二烯酸的合成以及作为细菌二氢二吡啶甲酸酯合酶抑制剂的二酯和二酸类似物的评价。酶动力学研究可以确定失活的二级速率常数。底物共孵育研究表明，抑制剂在活性位点起作用。质谱分析进一步探索了酶-抑制剂的相互作用并确定了酶烷基化的位点。

  DOI：

  10.1016/j.bmc.2008.10.026

文献信息

• New benzo [d] thiazole derivatives, process for their preparation and
  申请人：Laboratoires Jacques Logeais

  公开号：US04208420A1

  公开（公告）日：1980-06-17

  This invention relates to compounds having the general formula: ##STR1## and their pharmaceutically acceptable acid addition salts having the formula: ##STR2## in which: R represents hydrogen or a C.sub.1-4 alkyl radical, R' represents hydrogen or a C.sub.1-4 alkyl radical, m is 0, 1, 2 or 3, n is 3, 2, 1 or 0, the sum m+n being always equal to 3, and X.sup.- represents an anion formed by a pharmaceutically acceptable acid. Said compounds are typically useful as analgesic agents and as stimulants of the sympathetic nervous system, and also as central and peripheral vasoregulator agents.

  本发明涉及具有以下通式的化合物：##STR1##以及其药学上可接受的酸加合盐，其式为：##STR2##其中：R代表氢或C.sub.1-4烷基基团，R'代表氢或C.sub.1-4烷基基团，m为0、1、2或3，n为3、2、1或0，m+n之和始终等于3，X.sup.-代表由药学上可接受的酸形成的阴离子。这些化合物通常用作镇痛剂和交感神经系统的兴奋剂，以及中枢和周围血管调节剂。
• Discovery of potent liver-selective stearoyl-CoA desaturase-1 (SCD1) inhibitors, thiazole-4-acetic acid derivatives, for the treatment of diabetes, hepatic steatosis, and obesity
  作者：Tetsuya Iida、Minoru Ubukata、Ikuo Mitani、Yuichi Nakagawa、Katsuya Maeda、Hiroto Imai、Yosuke Ogoshi、Takahiro Hotta、Shohei Sakata、Ryuhei Sano、Hisayo Morinaga、Tamotsu Negoro、Shinichi Oshida、Masahiro Tanaka、Takashi Inaba

  DOI：10.1016/j.ejmech.2018.09.003

  日期：2018.10

  SCD1 is a rate-limiting enzyme in the conversion of saturated fatty acids to monounsaturated fatty acids. SCD1 inhibitors have potential effects on obesity, diabetes, acne, and cancer, but the adverse effects associated with SCD1 inhibition in the skin and eyelids are impediments to clinical development. To avoid mechanism-based adverse effects, we explored the compounds that selectively inhibit SCD1 in the liver in an ex vivo assay. Starting from a systemically active lead compound, we focused on the physicochemical properties tPSA and cLogP to minimize exposure in the off-target tissues. This effort led to the discovery of thiazole-4-acetic acid analog 48 as a potent and liver-selective SCD1 inhibitor. Compound 48 exhibited significant effects in rodent models of diabetes, hepatic steatosis, and obesity, with sufficient safety margins in a rat toxicology study with repeated dosing. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Two new irreversible inhibitors of dihydrodipicolinate synthase: diethyl (E,E)-4-oxo-2,5-heptadienedioate and diethyl (E)-4-oxo-2-heptenedioate
  作者：Jennifer J. Turner、Jackie P. Healy、Renwick C.J. Dobson、Juliet A. Gerrard、Craig A. Hutton

  DOI：10.1016/j.bmcl.2004.12.043

  日期：2005.2

  Dihydrodipicolinate synthase (DHDPS) is a key enzyme in lysine biosynthesis and an important antibiotic target. The enzyme catalyses the condensation of (S)-aspartate semialdehyde (ASA) and pyruvate to form dihydrodipicolinate. Two new irreversible inhibitors of dihydrodipicolinate synthase are reported, designed to mimic the acyclic enzyme-bound condensation product of ASA and pyruvate. These compounds represent an important new lead in the design of potent inhibitors for this enzyme. (C) 2004 Elsevier Ltd. All rights reserved.
• US4208420A
  申请人：——

  公开号：US4208420A

  公开（公告）日：1980-06-17