(R)-1,2,3,4-四氢-3-异喹啉羧酸甲酯 | 191327-28-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (R)-1,2,3,4-四氢-3-异喹啉羧酸甲酯
• 中文别名: 1,2,3,4-四氢异喹啉-3(R)-羧酸甲酯
• 英文名称: methyl (R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylate
• 英文别名: (R)-methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate；methyl (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
• CAS: 191327-28-3
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: YTNGWXICCHJHKA-SNVBAGLBSA-N

物化性质

• 沸点：
  298.0±28.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  (R)-1,2,3,4-四氢-3-异喹啉羧酸甲酯 在 ammonium hydroxide 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 72.0h， 生成 (±)-2-isopropyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
  参考文献：
  名称：

  Advances in Sulfonamide Kappa Opioid Receptor Antagonists: Structural Refinement and Evaluation of CNS Clearance

  摘要：

  DOI：

  10.1021/acschemneuro.2c00140
• 作为产物：
  描述：

  (R)-(+)-1,2,3,4-四氢异喹啉-3-羧酸 在 sodium hydroxide 、 caesium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 13.17h， 生成 (R)-1,2,3,4-四氢-3-异喹啉羧酸甲酯
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of Tic-hydantoin derivatives as selective σ1 ligands. Part 1

  摘要：

  Herein is described a new class of selective sigma(1), ligands consisting of tetrahydroisoquinoline-hydantoin (Tic-hydantoin) derivatives. Compound 3a has high affinity (IC50 = 16 nM) for the (71 receptor and is selective in a large panel of therapeutic targets. This first study presents structural changes around the Tic-hydantoin core, leading to a Tic-hydantoin analogue with a higher sigma(1) affinity (IC50 approximate to 1 nM). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.040

文献信息

• [EN] SUBSTITUTED SULFONAMIDES USEFUL AS ANTIAPOPTOTIC BCL INHIBITORS<br/>[FR] SULFONAMIDES SUBSTITUÉS UTILES COMME INHIBITEURS DE BCL ANTI-APOPTOTIQUES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012162365A1

  公开（公告）日：2012-11-29

  Disclosed are compounds of Formula (I), or a pharmaceutically acceptable salt thereof, wherein: W and Q and G are defined herein. Also disclosed are methods of using such compounds as inhibitors of Bcl-2 family antiapoptotic proteins for the treatment of cancer; and pharmaceutical compositions comprising such compounds.

  揭示了式（I）的化合物或其药学上可接受的盐，其中：W、Q和G在此处被定义。还揭示了将这些化合物用作Bcl-2家族抗凋亡蛋白的抑制剂以治疗癌症的方法；以及包含这些化合物的药物组合物。
• Cyclic and heterocyclic N-substituted &agr;-iminohydroxamic and carboxyclic acids
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US06207672B1

  公开（公告）日：2001-03-27

  Compounds of the formula I are suitable for preparing pharmaceuticals for the treatment of disorders in the course of which is involved an increased activity of matrix-degrading metalloproteinases.

  式I的化合物适用于制备用于治疗在其中涉及基质降解金属蛋白酶活性增加的疾病的药物。
• Cyclic and heterocyclic N-substituted alpha-iminohydroxamic and -carboxylic acids
  申请人：Hoechst Aktiengesellschaft

  公开号：US20010011134A1

  公开（公告）日：2001-08-02

  Cyclic and heterocyclic N-substituted &agr;-iminohydroxamic and -carboxylic acids Compounds of the formula I 1 are suitable for preparing pharmaceuticals for the treatment of disorders in the course of which is involved an increased activity of matrix-degrading metalloproteinases.

  公式I1的环状和杂环N-取代α-亚氨基羟酰胺和-羧酸化合物，适用于制备用于治疗涉及基质降解金属蛋白酶活性增加的疾病的药物。
• Cobalt‐Catalyzed Asymmetric Deuteration of α‐Amidoacrylates for Stereoselective Synthesis of α,β‐Dideuterated α‐Amino Acids
  作者：Aibo Li、Xinjian Song、Qiao Ren、Peiwang Bao、Xinyu Long、Fuli Huang、Lvjiang Yuan、Jianrong Steve Zhou、Xurong Qin

  DOI：10.1002/anie.202301091

  日期：——

  A cobalt-catalyzed enantioselective deuteration provides α,β-dideuterio-α-amino acids in excellent enantioselectivity and almost complete deuteration, using deuterated methanol as cheap deuterium source.

  使用氘化甲醇作为廉价的氘源，钴催化的对映选择性氘化以优异的对映选择性和几乎完全的氘化提供 α,β-二氘-α-氨基酸。
• New Type of Metalloproteinase Inhibitor:  Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids
  作者：Masaaki Sawa、Takao Kiyoi、Kiriko Kurokawa、Hiroshi Kumihara、Minoru Yamamoto、Tomohiro Miyasaka、Yasuko Ito、Ryoichi Hirayama、Tomomi Inoue、Yasuyuki Kirii、Eiji Nishiwaki、Hiroshi Ohmoto、Yu Maeda、Etsuko Ishibushi、Yoshimasa Inoue、Kohichiro Yoshino、Hirosato Kondo

  DOI：10.1021/jm0103211

  日期：2002.2.1

  A series of phosphonamide-based hydroxamate derivatives were synthesized, and the inhibitory activities were evaluated against various metalloproteinases in order to clarify its selectivity profile. Among the four diastereomeric isomers resulting from the chirality at the C-3 and P atoms, the compound with a (R,R)-configuration both at the C-3 position and the phosphorus atom was found to be potently active, while the other diastereomeric isomers were almost inactive. A number of (R,R)-compounds synthesized here exhibited broad spectrum activities with nanomolar K-i values against MMP-1, -3, -9, and TACE and also showed nanomolar IC50 values against HB-EGF shedding in a cell-based inhibition assay. The modeling study using X-ray structure of MMP-3 suggested the possible binding mode of the phosphonamide-based inhibitors.