(4R)-4-t-butoxycarbonylamino-5-hydroxypentanoic acid ethyl ester | 597577-78-1

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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
• 英文名称: (4R)-4-t-butoxycarbonylamino-5-hydroxypentanoic acid ethyl ester
• 英文别名: (4R)-5-hydroxy-4-t-butoxycarbonylaminopentanoic acid ethyl ester；(R)-4-Boc-amino-5-hydroxypentanoic acid ethyl ester；(R)-4-t-butoxycarbonylamino-5-hydroxy-pentanoic acid ethyl ester；(4R)-4-[[(1,1-Dimethylethoxy)carbonyl]amino]-5-hydroxypentanoic acid ethyl ester；ethyl (4R)-5-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 597577-78-1
• 化学式: C₁₂H₂₃NO₅
• 分子量: 261.318
• InChiKey: YJJLBIIKYNSDRO-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R)-4-t-butoxycarbonylamino-5-hydroxypentanoic acid ethyl ester 在 盐酸 、 硼烷四氢呋喃络合物 、 草酰氯 、 sodium hydride 、 二甲基亚砜 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 反应 28.75h， 生成 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester
  参考文献：
  名称：

  Discovery of novel prostaglandin analogs as potent and selective EP2/EP4 dual agonists

  摘要：

  To identify potent EP2/EP4 dual agonists with excellent subtype selectivity, a series of c-lactam prostaglandin E analogs bearing a 16-phenyl x-chain were synthesized and evaluated. Structural hybridization of 1 and 2, followed by more detailed chemical modification of the benzoic acid moiety, led us to the discovery of a 2-mercaptothiazole-4-carboxylic acid analog 3 as the optimal compound in the series. An isomer of this compound, the 2-mercaptothiazole-5-carboxylic acid analog 13, showed 34-fold and 13-fold less potent EP2 and EP4 receptor affinities, respectively. Structure activity relationship data from an in vitro mouse receptor binding assay are presented. Continued evaluation in an in vivo rat model of another 2-mercaptothiazole-4-carboxylic acid analog 17, optimized for sustained compound release from PLGA microspheres, demonstrated its effectiveness in a rat bone fracture-healing model following topical administration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.018
• 作为产物：
  描述：

  N-Boc-D-glutamic acid γ-ethyl ester 在 吡啶 、 锂硼氢 、 氯化亚砜 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (4R)-4-t-butoxycarbonylamino-5-hydroxypentanoic acid ethyl ester
  参考文献：
  名称：

  Discovery of a novel EP2/EP4 dual agonist with high subtype-selectivity

  摘要：

  A series of gamma-lactam prostaglandin E(1) analogs bearing a 16-phenyl moiety in the omega-chain and aryl moiety in the alpha-chain were synthesized and biologically evaluated. Among the tested compounds, gamma-lactam PGE analog 3 designed as a structural hybrid of 1 and 2 was discovered as the most optimized EP2/EP4 dual agonist with excellent subtype-selectivity (K(i) values: mEP2 = 9.3 nM, mEP4 = 0.41 nM). A structure-activity relationship study is presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.109

文献信息

• INDOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS
  申请人：Kim Soon Ha

  公开号：US20100210647A1

  公开（公告）日：2010-08-19

  The present invention relates to new indole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole compounds as an active ingredient.

  本发明涉及新的吲哚化合物，其药学上可接受的盐或异构体，用于预防或治疗细胞坏死和坏死相关疾病。本发明还涉及一种预防或治疗细胞坏死和坏死相关疾病的方法和组合物，该组合物包括所述吲哚化合物作为活性成分。
• [EN] INDOLE COMPOUNDS AS AN INHIBITOR OF CELLULAR NECROSIS<br/>[FR] COMPOSÉS D'INDOLE EN TANT QU'INHIBITEURS DE NÉCROSE CELLULAIRE
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2009025477A1

  公开（公告）日：2009-02-26

  The present invention relates to new indole compounds, pharmaceutically acceptable salts or isomers thereof which are useful for the prevention or treatment of cellular necrosis and necrosis-associated diseases. The present invention also relates to a method and a composition for the prevention or treatment of cellular necrosis and necrosis-associated diseases, comprising said indole compounds as an active ingredient.

  本发明涉及新的吲哚化合物、药学上可接受的盐或其异构体，用于预防或治疗细胞坏死和坏死相关疾病。本发明还涉及一种预防或治疗细胞坏死和坏死相关疾病的方法和组合物，其包括所述吲哚化合物作为活性成分。
• GLUCOKINASE ACTIVATORS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE INGREDIENT
  申请人：Kim Soon Ha

  公开号：US20100267708A1

  公开（公告）日：2010-10-21

  The present invention relates to new compounds of formula (1) exhibiting excellent activity for glucokinase, and pharmaceutical compositions comprising the same as an active ingredient.

  本发明涉及公式（1）的新化合物，表现出对葡萄糖激酶的优异活性，并且包括该化合物作为活性成分的药物组合物。
• INDOLE AND INDAZOLE DERIVATIVES HAVING A CELL-, TISSUE- AND ORGAN-PRESERVING EFFECT
  申请人：Kim Soon Ha

  公开号：US20100291533A1

  公开（公告）日：2010-11-18

  The present invention relates to a composition for preserving cells, tissues and organs, comprising as an active ingredient indole and indazole compounds of formula (1), or a pharmaceutically acceptable salt or isomer thereof, which are effective for preventing injury of organs, isolated cell systems or tissues caused by cold storage, transplant operation or post-transplantation reperfusion; a preservation method; and a preparation method of the composition.

  本发明涉及一种用于保存细胞、组织和器官的组合物，其中包括作为活性成分的式（1）的吲哚和吲唑化合物，或其药用可接受的盐或异构体，对于预防由冷藏、移植手术或移植后再灌注引起的器官、分离的细胞系统或组织的损伤具有有效性；一种保存方法；以及该组合物的制备方法。
• 8-Azaprostaglandin derivative compounds and drugs containing the compounds as the active ingredient
  申请人：Tani Kousuke

  公开号：US20050124577A1

  公开（公告）日：2005-06-09

  An 8-azaprostaglandin represented by formula (I) (wherein all symbols have the same meanings as described in the specification), a pharmaceutically acceptable salt thereof or a cyclodextrin clathrate thereof. Since the compound represented by formula (I) binds to EP2 subtype among PGE receptor strongly, it is useful for preventive and/or treatment for immune diseases, allergic diseases, neuronal cell death, dysmenorrhea, premature birth, abortion, baldness, retinal neuropathy such as glaucoma, erectile dysfunction, arthritis, pulmonary injury, pulmonary fibrosis, pulmonary emphysema, bronchitis, chronic obstructive pulmonary disease, hepatic injury, acute hepatitis, liver cirrhosis, shock, nephritis, renal failure, circulatory diseases, systemic inflammatory response syndrome, sepsis, hemophagocytosis syndrome, macrophage activation syndrome, still disease, Kawasaki Disease, burn, systemic granuloma, ulcerative colitis, Crohn disease, hypercytokinemia at dialysis, multiple organ failure, or bone diseases etc.

  一种由式(I)所表示的8-氮杂前列腺素，其中所有符号的含义与说明书中描述的相同，其药学上可接受的盐或环糊精包合物。由于式(I)所表示的化合物强烈结合到PGE受体中的EP2亚型，因此它对于预防和/或治疗免疫性疾病、过敏性疾病、神经元细胞死亡、痛经、早产、流产、脱发、青光眼等视网膜神经病变、勃起功能障碍、关节炎、肺损伤、肺纤维化、肺气肿、支气管炎、慢性阻塞性肺疾病、肝损伤、急性肝炎、肝硬化、休克、肾炎、肾功能衰竭、循环系统疾病、全身性炎症反应综合征、脓毒症、吞噬细胞过多综合征、巨噬细胞激活综合征、斯蒂尔病、川崎病、烧伤、全身性肉芽肿、溃疡性结肠炎、克隆氏病、透析时的高细胞因子血症、多器官衰竭或骨疾病等方面具有用途。