3(S)-(pyrid-3-yl)-β-alanine ethyl ester | 149519-95-9

• 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: 3(S)-(pyrid-3-yl)-β-alanine ethyl ester
• 英文别名: (S)-Ethyl β-amino-3-pyridinepropionate；ethyl 3(S)-3-amino-3-pyridin-3-ylpropanoate；ethyl (S)-3-amino-3-(3-pyridyl)propanoate；ethyl (3S)-3-amino-3-pyridin-3-ylpropanoate
• CAS: 149519-95-9
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: SUOOQSWLTJJSDK-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3(S)-(pyrid-3-yl)-β-alanine ethyl ester 在 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 生成 (S)-3-(2-{tert-Butoxycarbonyl-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-amino}-ethylamino)-3-pyridin-3-yl-propionic acid ethyl ester
  参考文献：
  名称：

  Nonpeptide α_vβ₃ Antagonists. 8. In Vitro and in Vivo Evaluation of a Potent α_vβ₃ Antagonist for the Prevention and Treatment of Osteoporosis

  摘要：

  3(S)-(6-Methoxypyridin-3-yl)-3-{2-oxo-3-[3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)propyl]-imidazolidin-1-yl}propionic acid 6 was identified as a potent and selective antagonist of the alpha(v)beta(3) receptor. This compound has an excellent in vitro profile (IC50 = 0.08 nM), a significant unbound fraction in human plasma (12%), and good pharmacokinetics in rat, dog, and rhesus monkey. On the basis of the efficacy shown in three in vivo models of bone turnover, the compound was selected for clinical development. To support the ongoing metabolism and safety studies, a novel strategy was employed in which a series of oxidized derivatives of 6 were prepared by exposure of 6 (or the methyl ester) to chemical oxidizing agents. These products proved useful in the identification of active metabolites generated by either in vitro or in vivo metabolism.

  DOI：

  10.1021/jm030306r
• 作为产物：
  描述：

  3-溴吡啶 在 palladium dihydroxide 正丁基锂 、 氢气 、 palladium diacetate 、 溶剂黄146 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 乙腈 为溶剂， 生成 3(S)-(pyrid-3-yl)-β-alanine ethyl ester
  参考文献：
  名称：

  Nonpeptide α_vβ₃ Antagonists. 8. In Vitro and in Vivo Evaluation of a Potent α_vβ₃ Antagonist for the Prevention and Treatment of Osteoporosis

  摘要：

  3(S)-(6-Methoxypyridin-3-yl)-3-{2-oxo-3-[3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)propyl]-imidazolidin-1-yl}propionic acid 6 was identified as a potent and selective antagonist of the alpha(v)beta(3) receptor. This compound has an excellent in vitro profile (IC50 = 0.08 nM), a significant unbound fraction in human plasma (12%), and good pharmacokinetics in rat, dog, and rhesus monkey. On the basis of the efficacy shown in three in vivo models of bone turnover, the compound was selected for clinical development. To support the ongoing metabolism and safety studies, a novel strategy was employed in which a series of oxidized derivatives of 6 were prepared by exposure of 6 (or the methyl ester) to chemical oxidizing agents. These products proved useful in the identification of active metabolites generated by either in vitro or in vivo metabolism.

  DOI：

  10.1021/jm030306r

文献信息

• Nonpeptide αvβ3 antagonists. Part 2: constrained glycyl amides derived from the RGD tripeptide
  作者：Robert S. Meissner、James J. Perkins、Le T. Duong、George D. Hartman、William F. Hoffman、Joel R. Huff、Nathan C. Ihle、Chih-Tai Leu、Rose M. Nagy、Adel Naylor-Olsen、Gideon A. Rodan、Sevgi B. Rodan、David B. Whitman、Gregg A. Wesolowski、Mark E. Duggan

  DOI：10.1016/s0960-894x(01)00687-4

  日期：2002.1

  the RGD tripeptide are described that are potent, selective antagonists of the integrin receptor, alpha(v)beta(3). The use of the 5,6,7,8-tetrahydro[1,8]naphthyridine group as a potency-enhancing N-terminus is demonstrated. Two 3-substituted-3-amino-propionic acids previously contained in alpha(IIb)beta(3) antagonists were utilized to enhance binding affinity and functional activity for the targeted

  描述了RGD三肽的模拟物，它们是整联蛋白受体α（v）beta（3）的有效选择性拮抗剂。证明了使用5,6,7,8-四氢[1,8]萘啶基作为增强效价的N-末端。以前包含在alpha（IIb）beta（3）拮抗剂中的两个3-取代的-3-氨基丙酸被用来增强对目标受体的结合亲和力和功能活性。然后，通过使用环状缩水甘油酰胺键约束，进一步提高了亲和力。
• 4 -HYDROXY- ISOQUINOLINE COMPOUNDS AS HIF HYDROXYLASE INHIBITORS
  申请人：FIBROGEN, INC.

  公开号：US20150038528A1

  公开（公告）日：2015-02-05

  The present invention relates to novel compounds of formula (I), and compositions capable of inhibiting PHD1 enzyme activity selectively over other isoforms, for example, PHD2 and/or PHD3 enzymes. The invention also relates to compounds of formula (I) for use in disorders such as muscle degeneration, colitis, IBD, and certain ischemias.

  本发明涉及公式（I）的新型化合物及其组合物，能够选择性地抑制PHD1酶活性，而不影响其他同工酶，例如PHD2和/或PHD3酶。本发明还涉及公式（I）的化合物在肌肉退化、结肠炎、炎症性肠病和某些缺血症等疾病中的使用。
• Burkholderia cepacia lipase is an excellent enzyme for the enantioselective hydrolysis of β-heteroaryl-β-amino esters
  作者：Gábor Tasnádi、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2009.06.019

  日期：2009.8

  The enantioselective (E > 200) lipase PS-catalysed hydrolysis of beta-heteroaryl-beta-amino esters is described. The reactions were performed with H2O (0.5 equiv) in either diisopropyl ether or tert-butyl methyl ether at 25 degrees C. The resulting beta-heteroaryl-substituted beta-amino acid enantiomers were formed in high enantiomeric excess (ee >= 97%) and in good yield (>= 40%). (c) 2009 Elsevier Ltd. All rights reserved.
• A highly stereoselective Michael addition to an .alpha.,.beta.-unsaturated ester as the crucial step in the synthesis of a novel .beta.-amino acid-containing fibrinogen receptor antagonist
  作者：Joseph G. Rico、Richard J. Lindmark、Thomas E. Rogers、Philippe R. Bovy

  DOI：10.1021/jo00079a054

  日期：1993.12
• US6506744B1
  申请人：——

  公开号：US6506744B1

  公开（公告）日：2003-01-14