(2R,3R)-4-(benzyloxy)-2,3-dihydroxy-4-oxobutanoic acid | 122947-43-7

• 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: (2R,3R)-4-(benzyloxy)-2,3-dihydroxy-4-oxobutanoic acid
• 英文别名: (2R,3R)-2,3-Dihydroxy-succinic acid monobenzyl ester；(2R,3R)-2,3-dihydroxy-4-oxo-4-phenylmethoxybutanoic acid
• CAS: 122947-43-7
• 化学式: C₁₁H₁₂O₆
• 分子量: 240.213
• InChiKey: HNERUQGVRKFROS-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-二碘丙烷 、 (2R,3R)-4-(benzyloxy)-2,3-dihydroxy-4-oxobutanoic acid 在 四丁基氢氧化铵 作用下， 生成 (2S,3S)-2,3-Dihydroxy-succinic acid benzyl ester 3-((2R,3R)-3-benzyloxycarbonyl-2,3-dihydroxy-propionyloxy)-propyl ester
  参考文献：
  名称：

  Studies on the mechanism of the asymmetric epoxidation: a ligand variation approach

  摘要：

  DOI：

  10.1021/jo00278a004
• 作为产物：
  描述：

  Trifluoro-acetic acid (3R,4R)-2,5-dioxo-4-(2,2,2-trifluoro-acetoxy)-tetrahydro-furan-3-yl ester 、 苯甲醇 以 四氢呋喃 为溶剂， 反应 4.0h， 以38%的产率得到(2R,3R)-4-(benzyloxy)-2,3-dihydroxy-4-oxobutanoic acid
  参考文献：
  名称：

  [EN] TARTARIC ACID ANALOGS AND USES THEREOF
  [FR] ANALOGUES D'ACIDE TARTRIQUE ET LEURS UTILISATIONS

  摘要：

  Provided herein are tartaric acid analogs represented by the following structural formula: or a pharmaceutically acceptable salt thereof, wherein values for the variables (e.g., A, R) are as described herein. Compounds of structural formula I and pharmaceutically acceptable salts thereof are believed to be useful in overcoming tumor resistance and promoting an immune response. Accordingly, also provided herein are various methods involving compounds of structural formula I, e.g., methods of treating a cancer in a subject in need thereof.

  公开号：

  WO2022165511A1

文献信息

• SUBSTITUTED PROPIONYL DERIVATIVES
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP0949238A1

  公开（公告）日：1999-10-13

  The present invention relates to a compound represented by the following formula (1): [wherein, X1 represents a carboxyl group which may be esterified or the like group; Y1 represents a single bond, -O- or -N(R1)-; at least one of A1, A2 and A3 is a group represented by the following formula (2): -R2-a1-R3-a2 →wherein, R2 represents a divalent C2-12 hydrocarbon group, R3 represents a single bond or a divalent C1-12 hydrocarbon group, a1 and a2 individually represent a single bond, -S-, -SO-, -SO2-, -SO2NH-, -O-, -N(R4)-, -CON(R5)-, -C(=O)- or - Si(R6)(R7)- and → means bonding with Q1, Q2 or Q3}, the remaining one or two of A1, A2 and A3 are the same or different and each independently represents a group represented by the following formula (3): -R8-a3-R9-a4 →wherein, R8 and R9 individually represent a single bond or a divalent C1-12 hydrocarbon group, a3 and a4 individually represent a single bond, -S-, -SO-, -SO2-, -SO2NH-, -O-, - N(R10)-, -CON(R11)-, -C(=O)- or -SI(R12)(R13)- and → means bonding with Q1, Q2 or Q3},; at least one of Q1, Q2 and Q3 represents a cyclic hydrocarbon group or heterocyclic group and the remaining one or two of Q1, Q2 and Q3 individually represent a hydrogen atom, a carboxyl group which may be esterified, a hydrocarbon group or a heterocyclic group] or salt thereof; and a pharmaceutical comprising the same as an effective ingredient. The compound exhibits strong squalene synthetase inhibitory action and is therefore useful as a pharmaceutical for the treatment·prevention of hypercholesterolemia, hyperlipemia or arteriosclerosis.

  本发明涉及一种由以下式（1）表示的化合物：[其中，X1代表可能酯化或类似基团的羧基；Y1代表单键，-O-或-N（R1）-；A1、A2和A3中至少有一个是由以下式（2）表示的基团：-R2-a1-R3-a2 →其中，R2代表二价的C2-12碳氢基团，R3代表单键或二价的C1-12碳氢基团，a1和a2分别代表单键，-S-，-SO-，-SO2-，-SO2NH-，-O-，-N（R4）-，-CON（R5）-，-C（=O）-或-Si（R6）（R7）-，→表示与Q1、Q2或Q3结合}，A1、A2和A3中剩余的一个或两个是相同或不同的，并且每个独立地表示由以下式（3）表示的基团：-R8-a3-R9-a4 →其中，R8和R9分别代表单键或二价的C1-12碳氢基团，a3和a4分别代表单键，-S-，-SO-，-SO2-，-SO2NH-，-O-，-N（R10）-，-CON（R11）-，-C（=O）-或-SI（R12）（R13）-，→表示与Q1、Q2或Q3结合}；Q1、Q2和Q3中至少有一个代表环烃基或杂环烃基，剩余的一个或两个分别代表氢原子，可能酯化的羧基，碳氢基团或杂环烃基的其中一个或两个]或其盐；以及包括其作为有效成分的药物。该化合物表现出强烈的角鲨烯合酶抑制作用，因此可用作治疗高胆固醇血症、高脂血症或动脉硬化的药物。
• Amino sugar derivatives
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP0563908A1

  公开（公告）日：1993-10-06

  A compound represented by formula (I): wherein R¹ represents -CO-Z¹-N(Z¹¹)-CO-Z²-H or -CO-Z³-H, wherein Z¹, Z², and Z³ each represent an alkylene group having from 1 to 20 carbon atoms, a phenylene group, or a combination thereof, and Z¹¹ represents a hydrogen atom, an alkyl group having from 1 to 20 carbon atoms which may be substituted with a phenyl group, a phenyl group which may be substituted with an alkyl group having from 1 to 20 carbon atoms, or an alkylene group having from 1 to 20 carbon atoms which may contain therein a phenylene group; R² represents -CO-Z⁴-N(Z¹²)-CO-Z⁵-H, -CO-Z⁶-H or a hydrogen atom, wherein Z⁴, Z⁵, and Z⁶ each have the same meaning as Z¹, and Z¹² has the same meaning as Z¹¹; Q¹ and Q² each represent a carboxyl group or a phosphonoxy group; Q³ represents a hydrogen atom, a carboxyl group or a phosphonoxy group; m represents 0 or an integer of from 1 to 20; n represents 0 or an integer of from 1 to 20; Y¹ represents an alkylene group having from 1 to 10 carbon atoms which may contain one or more substituents selected from -OCOR¹¹ and -NHCOR¹², wherein R¹¹ represents -Z¹³ or -Z⁷-N(Z¹⁴)-CO-Z⁸-H (wherein Z⁷ and Z⁸ each have the same meaning as Z¹, and Z¹³ and Z¹⁴ each have the same meaning as Z¹¹) and R¹² represents -Z¹⁵ or -Z⁹-N(Z¹⁶)-CO-Z¹⁰-H (wherein Z⁹ and Z¹⁰ each have the same meaning as Z¹, and Z¹⁵ and Z¹⁶ each have the same meaning as Z¹¹), and a salt thereof. The compound inhibits TNF derivation by endotoxin and is therefore useful for the treatment of multiorganic insufficiencies.

  式 (I) 所代表的化合物： 其中 R¹ 代表-CO-Z¹-N(Z¹¹)-CO-Z²-H 或 -CO-Z³-H，其中 Z¹、Z² 和 Z³ 分别代表具有 1 至 20 个碳原子的亚烷基、亚苯基或它们的组合，而 Z¹¹ 代表氢原子、可被苯基取代的具有 1 至 20 个碳原子的烷基，可被具有 1 至 20 个碳原子的烷基取代的苯基，或具有 1 至 20 个碳原子的亚烷基，其中可含有亚苯基；R²代表-CO-Z⁴-N(Z¹²)-CO-Z⁵-H、-CO-Z⁶-H或氢原子，其中Z⁴、Z⁵和Z⁶各自与Z¹含义相同，Z¹²与Z¹含义相同；Q¹ 和 Q² 各自代表羧基或膦酰氧基；Q³ 代表氢原子、羧基或膦酰氧基；m 代表 0 或 1 至 20 的整数；n 代表 0 或 1 至 20 的整数；Y¹ 代表具有 1 至 10 个碳原子的亚烷基，该亚烷基可包含一个或多个选自 -OCOR¹¹ 和 -NHCOR¹² 的取代基，其中 R¹¹ 代表 -Z¹³ 或 -Z⁷-N(Z¹⁴)-CO-Z⁸-H (其中 Z⁷ 和 Z⁸ 各自与 Z¹、Z¹³和Z¹⁴各自与Z¹¹具有相同的含义）和R¹²代表-Z¹⁵或-Z⁹-N(Z¹⁶)-CO-Z¹⁰-H（其中Z⁹和Z¹⁰各自与Z¹¹具有相同的含义，Z¹⁵和Z¹⁶各自与Z¹¹具有相同的含义），及其盐。该化合物可抑制由内毒素衍生的 TNF，因此可用于治疗多器官功能不全。
• US5432267A
  申请人：——

  公开号：US5432267A

  公开（公告）日：1995-07-11
• Studies on the mechanism of the asymmetric epoxidation: a ligand variation approach
  作者：Paul R. Carlier、K. Barry Sharpless

  DOI：10.1021/jo00278a004

  日期：1989.8
• [EN] TARTARIC ACID ANALOGS AND USES THEREOF<br/>[FR] ANALOGUES D'ACIDE TARTRIQUE ET LEURS UTILISATIONS
  申请人：[en]LAPIX THERAPEUTICS, INC.

  公开号：WO2022165511A1

  公开（公告）日：2022-08-04

  Provided herein are tartaric acid analogs represented by the following structural formula: or a pharmaceutically acceptable salt thereof, wherein values for the variables (e.g., A, R) are as described herein. Compounds of structural formula I and pharmaceutically acceptable salts thereof are believed to be useful in overcoming tumor resistance and promoting an immune response. Accordingly, also provided herein are various methods involving compounds of structural formula I, e.g., methods of treating a cancer in a subject in need thereof.