(±)-methyl 3-phenyl-2-(1-trityl-1H-imidazol-4-yl)propanoate | 199007-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (±)-methyl 3-phenyl-2-(1-trityl-1H-imidazol-4-yl)propanoate
• 英文别名: Methyl 3-phenyl-2-(1-tritylimidazol-4-yl)propanoate
• CAS: 199007-39-1
• 化学式: C₃₂H₂₈N₂O₂
• 分子量: 472.587
• InChiKey: BRQVKODAWADGPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-methyl 3-phenyl-2-(1-trityl-1H-imidazol-4-yl)propanoate 在 水 、 氢溴酸 作用下， 反应 2.5h， 以88%的产率得到2-(1H-imidazol-4-yl)-3-phenylpropanoic acid
  参考文献：
  名称：

  发现α-取代的咪唑-4-乙酸类似物作为新型一类对视网膜血管音有影响的ρ1γ-氨基丁酸A型受体拮抗剂

  摘要：

  含ρ的γ-氨基丁酸A型受体（GABA A Rs）在控制视觉信号中起重要作用。因此，选择性靶向这些GABA A R的配体是令人关注的。在这项研究中，我们证明了部分GABA A R激动剂咪唑-4-乙酸（IAA）能够在体内穿透血脑屏障。我们制备了一系列的α-和N-烷基化以及IAA的双环类似物，以研究该支架的结构-活性关系，重点是IAA的乙酸侧链。通过IAA制备从化合物升通过有效最小步合成组氨酸，以及它们的药理学性质进行了表征在天然大鼠GABA甲Rs in a [3H]muscimol binding assay and at recombinant human α1β2γ2S and ρ1 GABAARs using the FLIPR™ membrane potential assay. The (+)‐α‐methyl‐ and α‐cyclopropyl‐substituted IAA analogues

  DOI：

  10.1002/cmdc.201600356
• 作为产物：
  描述：

  4-咪唑乙酸盐酸盐 在 硫酸 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (±)-methyl 3-phenyl-2-(1-trityl-1H-imidazol-4-yl)propanoate
  参考文献：
  名称：

  A new type of carboxypeptidase a inhibitors designed using an imidazole as a zinc coordinating ligand

  摘要：

  2-(4-Imidazoyl)hydrocinnamic acid (1) and its congeners (2-4) having different length of alkyl chain spacers between the imidazole ring and the a-carbon to the carboxylate of 1 have been designed, synthesized and evaluated as inhibitors for carboxypeptidase A to show that they are competitive inhibitors for the enzyme. Inhibitor 1 was most potent having the K-i value of 0.8 mu M. The present study demonstrates that imidazole ring is an effective zinc coordinating ligand that can be useful for the design of inhibitors for zinc proteases. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00134-x

文献信息

• PRENYL TRANSFERASE INHIBITORS
  申请人：SOCIETE DE CONSEILS DE RECHERCHESET D'APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.)

  公开号：EP1140942A2

  公开（公告）日：2001-10-10
• [EN] PRENYL TRANSFERASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PRENYL-TRANSFERASE
  申请人：SOD CONSEILS RECH APPLIC

  公开号：WO2000039130A2

  公开（公告）日：2000-07-06

  A family of imidazole compounds useful for inhibiting the activity of prenyl transferases. The compounds are covered by formula (I): wherein X is (CHR11)n3(CH2)n4Z(CH2)n5 where Z is O, N(R12), S, or a bond; Y is CO, CH¿2?, CS, or a bond; R?1¿ is A, B, C, D, E, F, G, H, I, J or N(R24R25); and the remaining substituents are as defined in the disclosure.
• A new type of carboxypeptidase a inhibitors designed using an imidazole as a zinc coordinating ligand
  作者：Kyung Joo Lee、Keum Chan Joo、Eun-Jung Kim、Mijoon Lee、Dong H Kim

  DOI：10.1016/s0968-0896(97)00134-x

  日期：1997.10

  2-(4-Imidazoyl)hydrocinnamic acid (1) and its congeners (2-4) having different length of alkyl chain spacers between the imidazole ring and the a-carbon to the carboxylate of 1 have been designed, synthesized and evaluated as inhibitors for carboxypeptidase A to show that they are competitive inhibitors for the enzyme. Inhibitor 1 was most potent having the K-i value of 0.8 mu M. The present study demonstrates that imidazole ring is an effective zinc coordinating ligand that can be useful for the design of inhibitors for zinc proteases. (C) 1997 Elsevier Science Ltd.
• Discovery of α-Substituted Imidazole-4-acetic Acid Analogues as a Novel Class of ρ₁γ-Aminobutyric Acid Type A Receptor Antagonists with Effect on Retinal Vascular Tone
  作者：Jacob Krall、Benjamin M. Brygger、Sara B. Sigurðardóttir、Clarissa K. L. Ng、Christoffer Bundgaard、Jan Kehler、Birgitte Nielsen、Toke Bek、Anders A. Jensen、Bente Frølund

  DOI：10.1002/cmdc.201600356

  日期：2016.10.19

  of α‐ and N‐alkylated, as well as bicyclic analogues of IAA to explore the structure–activity relationship of this scaffold focusing on the acetic acid side chain of IAA. The compounds were prepared via IAA from l‐histidine by an efficient minimal‐step synthesis, and their pharmacological properties were characterized at native rat GABAARs in a [3H]muscimol binding assay and at recombinant human α1β2γ2S

  含ρ的γ-氨基丁酸A型受体（GABA A Rs）在控制视觉信号中起重要作用。因此，选择性靶向这些GABA A R的配体是令人关注的。在这项研究中，我们证明了部分GABA A R激动剂咪唑-4-乙酸（IAA）能够在体内穿透血脑屏障。我们制备了一系列的α-和N-烷基化以及IAA的双环类似物，以研究该支架的结构-活性关系，重点是IAA的乙酸侧链。通过IAA制备从化合物升通过有效最小步合成组氨酸，以及它们的药理学性质进行了表征在天然大鼠GABA甲Rs in a [3H]muscimol binding assay and at recombinant human α1β2γ2S and ρ1 GABAARs using the FLIPR™ membrane potential assay. The (+)‐α‐methyl‐ and α‐cyclopropyl‐substituted IAA analogues