(3R,4R)-4-氨基-3-羟基哌啶-1-羧酸苄酯 | 959617-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3R,4R)-4-氨基-3-羟基哌啶-1-羧酸苄酯
• 英文名称: benzyl (3R,4R)-4-amino-3-hydroxy-piperidine-1-carboxylate
• 英文别名: (rac)-(3R,4R)-4-amino-3-hydroxy-piperidine-1-carboxylic acid benzyl ester；Benzyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylate
• CAS: 959617-87-9
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: IRKGMFWANMCSOS-VXGBXAGGSA-N

物化性质

• 沸点：
  417.2±45.0 °C(Predicted)
• 密度：
  1.249

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  75.8
• 氢给体数：
  2
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  (3S,4S)-苄基4-氨基-3-羟基哌啶-1-羧酸酯	benzyl (3S,4S)-4-amino-3-hydroxy-piperidine-1-carboxylate	1007596-63-5	C13H18N2O3	250.298
  ——	trans(±)benzyl-4-azido-3-hydroxypiperidine-1-carboxylate	——	C13H16N4O3	276.295

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  (3R,4r)-苄基 4-(叔丁氧基羰基氨基)-3-羟基哌啶-1-羧酸	trans-benzyl 4-((tert-butoxycarbonyl)amino)-3-hydroxypiperidine-1-carboxylate	724787-53-5	C18H26N2O5	350.415
  ——	benzyl (3R,4R)-4-(benzhydrylideneamino)-3-hydroxy-piperidine-1-carboxylate	1007596-64-6	C26H26N2O3	414.504
  (3R,4R)-N-BOC-3-羟基-4-氨基哌啶	(3R,4R)-tert-butyl 4-amino-3-hydroxypiperidine-1-carboxylate	1007596-95-3	C10H20N2O3	216.28
  ——	benzyl (3S,4R)-4-amino-3-azidopiperidine-1-carboxylate	1007596-66-8	C13H17N5O2	275.31
  ——	tert-butyl (3R,4R)-4-[(diphenylmethylene)amino]-3-hydroxypiperidine-1-carboxylate	1007596-93-1	C23H28N2O3	380.487

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4-氨基-3-羟基哌啶-1-羧酸苄酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 26.0h， 生成 benzyl (3S,4R)-3-azido-4-(benzhydrylideneamino)piperidine-1-carboxylate
  参考文献：
  名称：

  Optimization of Pyrrolamide Topoisomerase II Inhibitors Toward Identification of an Antibacterial Clinical Candidate (AZD5099)

  摘要：

  AZD5099 (compound 63) is an antibacterial agent that entered phase 1 clinical trials targeting infections caused by Gram-positive and fastidious Gram-negative bacteria. It was derived from previously reported pyrrolamide antibacterials and a fragment-based approach targeting the ATP binding site of bacterial type II topoisomerases. The program described herein varied a 3-piperidine substituent and incorporated 4-thiazole substituents that form a seven-membered ring intramolecular hydrogen bond with a 5-position carboxylic acid. Improved antibacterial activity and lower in vivo clearances were achieved. The lower clearances were attributed, in part, to reduced recognition by the multidrug resistant transporter Mrp2. Compound 63 showed notable efficacy in a mouse neutropenic Staphylococcus aureus infection model. Resistance frequency versus the drug was low, and reports of clinical resistance due to alteration of the target are few. Hence, 63 could offer a novel treatment for serious issues of resistance to currently used antibacterials.

  DOI：

  10.1021/jm500462x
• 作为产物：
  描述：

  n-Carbobenzoxy-trans-3-hydroxy-4-azidopiperidine 在 钯 、 氢气 、 甲醇 、 silica gel 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 以to give 11.4 g (63%)的产率得到(3R,4R)-4-氨基-3-羟基哌啶-1-羧酸苄酯
  参考文献：
  名称：

  Antibacterial agents

  摘要：

  喹啉和萘啶衍生物可用于治疗哺乳动物（尤其是人类）的细菌感染。

  公开号：

  US20060041123A1
• 作为试剂：
  描述：

  (3R,4R)-N-BOC-3-羟基-4-氨基哌啶 、 二苯甲酮亚胺 、 、 三乙胺 在 (3R,4R)-4-氨基-3-羟基哌啶-1-羧酸苄酯 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以Isolation gave 2.8 g of the title compound in an overall 62% yield from Intermediate 74的产率得到tert-butyl (3R,4R)-4-[(diphenylmethylene)amino]-3-hydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  PYRROLE DERIVATIVES WITH ANTIBACTERIAL ACTIVITY

  摘要：

  本文描述了化学式（I）的化合物及其药用可接受的盐。还描述了制备它们的过程，含有它们的药物组合物，它们作为药物的用途以及它们在治疗细菌感染方面的用途。

  公开号：

  US20100286181A1

文献信息

• HALO-SUBSTITUTED PYRIMIDODIAZEPINES
  申请人：Cai Jianping

  公开号：US20090318408A1

  公开（公告）日：2009-12-24

  The present invention provides PLK1 inhibitor compounds of formula I: useful in the treatment or control of cell proliferative disorders, particularly oncological disorders. These compounds and formulations containing such compounds may be useful in the treatment or control of solid tumors, such as, for example, breast, colon, lung and prostate tumors and other oncological diseases such as non-Hodgkin's lymphomas. Also provided are intermediate compounds useful in the synthesis of compounds of formula I.

  本发明提供了公式I的PLK1抑制剂化合物： 用于治疗或控制细胞增殖性疾病，特别是肿瘤性疾病。这些化合物和含有这些化合物的配方可能在治疗或控制实体肿瘤方面有用，例如乳腺癌、结肠癌、肺癌和前列腺癌等固体肿瘤，以及非霍奇金淋巴瘤等其他肿瘤性疾病。还提供了在合成公式I化合物中有用的中间体化合物。
• SOMATOSTATIN MODULATORS AND USES THEREOF
  申请人：Crinetics Pharmaceuticals, Inc.

  公开号：US20180016252A1

  公开（公告）日：2018-01-18

  Described herein are compounds that are somatostatin modulators, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders that would benefit from modulation of somatostatin activity.

  本文描述了一些肽类调节剂化合物，制备这类化合物的方法，包含这类化合物的药物组合物和药物，以及利用这类化合物治疗需要调节生长抑素活性的疾病、症状或疾病的方法。
• INHIBITORS OF JAK
  申请人：de Vicente Fidalgo Javier

  公开号：US20110059118A1

  公开（公告）日：2011-03-10

  The present invention relates to the use of novel compounds of Formula I, wherein the variables m, n, p, q, Q, r, R, R′, X, X′, Y, Z 1 , Z 2 , and Z 3 are defined as described herein, which inhibit JAK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及使用式I的新化合物，其中变量m、n、p、q、Q、r、R、R′、X、X′、Y、Z1、Z2和Z3如本文所述定义，这些化合物抑制JAK并且对于治疗自身免疫和炎症性疾病有用。
• Antibacterial agents
  申请人：Axten MICHAEL Jeffrey

  公开号：US20060041123A1

  公开（公告）日：2006-02-23

  Quinoline and naphthyridine derivatives useful in the treatment of bacterial infections in mammals, particularly humans.

  喹啉和萘啶衍生物可用于治疗哺乳动物（尤其是人类）的细菌感染。
• SUBSTITUTED HETEROCYCLES AND THEIR USE AS CHK1, PDK1 AND PAK INHIBITORS
  申请人：Daly Kevin

  公开号：US20090275570A1

  公开（公告）日：2009-11-05

  The invention relates to novel compounds of Formula (I) and to their pharmaceutical compositions and to their methods of use. These novel compounds possess CHK1 kinase inhibitory activity, PDK1 inhibitory activity and Pak kinase inhibitory activity and are accordingly useful in the treatment and/or prophylaxis of cancer.

  本发明涉及新的化合物（I）及其药物组成物和使用方法。这些新的化合物具有CHK1激酶抑制活性，PDK1抑制活性和Pak激酶抑制活性，因此在癌症的治疗和/或预防中有用。