2-{1,2,3,4-tetrahydro-2-[(9H-fluoren-9-ylmethoxy)carbonyl]-1-isoquinolinyl}acetic acid | 540483-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-{1,2,3,4-tetrahydro-2-[(9H-fluoren-9-ylmethoxy)carbonyl]-1-isoquinolinyl}acetic acid
• 英文别名: 2-(2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)acetic acid；2-[2-(9H-fluoren-9-ylmethoxycarbonyl)-3,4-dihydro-1H-isoquinolin-1-yl]acetic acid
• CAS: 540483-55-4
• 化学式: C₂₆H₂₃NO₄
• 分子量: 413.473
• InChiKey: RHKMQYBFMUXKQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-苯乙胺 、 N-alpha-芴甲氧羰基-N-in-叔丁氧羰基-D-色氨酸 、 5-(9H-fluoren-9-ylmethoxy)-1,3,4-oxadiazol-2(3H)-one 、 2-{1,2,3,4-tetrahydro-2-[(9H-fluoren-9-ylmethoxy)carbonyl]-1-isoquinolinyl}acetic acid 生成 N1-(2-phenylethyl)-(2R)-2-{[N'-(2-(1,2,3,4-tetrahydro-1-isoquinolinyl)ethanoyl)hydrazino]carboxamido}-3-(1H-3-indolyl)propanamide
  参考文献：
  名称：

  Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3

  摘要：

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.

  DOI：

  10.1021/jm0210921
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 1,2,3,4-四氢异喹啉-1-乙酸 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 以79%的产率得到2-{1,2,3,4-tetrahydro-2-[(9H-fluoren-9-ylmethoxy)carbonyl]-1-isoquinolinyl}acetic acid
  参考文献：
  名称：

  Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3

  摘要：

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.

  DOI：

  10.1021/jm0210921

文献信息

• Isoquinoline derivatives
  申请人：Wiesner Matthias

  公开号：US20050090525A1

  公开（公告）日：2005-04-28

  Isoquinoline derivatives of the general formula (I) in which X, Y, Z, R 1 , R 2 , and n are as defined in Patent Claim ( 1 ), and physiologically acceptable salts or solvates thereof, are integrin inhibitors and can be employed for combating thromboses, cardiac infarction, coronary heart diseases, arteriosclerosis, inflammation, tumours, osteoporosis, infections and restenosis after angioplasty or in pathological processes which are maintained or propagated by angiogenesis.

  通式（I）中X，Y，Z，R1，R2和n的异喹啉衍生物，以及其生理上可接受的盐或溶剂，是整合素抑制剂，可用于对抗血栓、心肌梗死、冠心病、动脉硬化、炎症、肿瘤、骨质疏松症、感染以及血管新生维持或传播的病理过程中的再狭窄。
• ISOCHINOLINDERIVATE
  申请人：MERCK PATENT GmbH

  公开号：EP1480971A1

  公开（公告）日：2004-12-01
• US7060707B2
  申请人：——

  公开号：US7060707B2

  公开（公告）日：2006-06-13
• [DE] ISOCHINOLINDERIVATE<br/>[EN] ISOQUINOLINE DERIVATIVES<br/>[FR] DERIVES D'ISOQUINOLEINE
  申请人：MERCK PATENT GMBH

  公开号：WO2003074512A1

  公开（公告）日：2003-09-12

  Isochinolinderivate der allgemeinen Formel (I), worin X, Y, Z, R1, R2 und n, die in Patentanspruch (1) angegebenen Bedeutungen haben, sowie deren physiologisch unbedenklichen Salze oder Solvate sind Integrininhibitoren und können zur Bekämpfung von Thrombosen, Herzinfarkt, koronaren Herzerkrankungen, Arteriosklerose, Entzündungen, Tumoren, Osteoporose, Infektionen und Restenose nach Angioplastie oder bei pathologischen Vorgängen, die durch Angiogenese unterhalten oder propagiert werden, eingesetzt werden.
• Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3
  作者：Dirk Weber、Claudia Berger、Peter Eickelmann、Jochen Antel、Horst Kessler

  DOI：10.1021/jm0210921

  日期：2003.5.1

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.