methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2'-bromophenyl)propanoate

• 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: methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2'-bromophenyl)propanoate
• 英文别名: (S)-methyl 3-(2-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate；methyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-2-bromo-L-phenylalaninate；methyl (2S)-3-(2-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoate；methyl (2S)-3-(2-bromophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• 化学式: C₁₅H₂₀BrNO₄
• 分子量: 358.232
• InChiKey: GVCWQKAEBHIGJA-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2'-bromophenyl)propanoate 在 tris(dibenzylideneacetone)dipalladium (0) 、 三(邻甲基苯基)磷 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以87%的产率得到methyl (S)-N-(tert-butoxycarbonyl)indoline-2-carboxylate
  参考文献：
  名称：

  Synthesis of 2-substituted indolines using sequential Pd-catalyzed processesElectronic supplementary information (ESI) available: 1H and 13C NMR spectra for all products without elemental analysis data (3c–g and 4d–g). See http://www.rsc.org/suppdata/p1/b2/b200163b/

  摘要：

  通过钯催化氨基官能化有机锌试剂与 2-溴碘苯偶联，然后进行布赫瓦尔德钯催化分子内胺化反应，开发出了一条制备对映体纯度为 2-取代吲哚类化合物 4a-g 和 2-取代四氢喹啉 4h 的简便路线。初始偶联的收率不高（36-52%），但环化收率令人满意（63-87%）。通过手性相高效液相色谱法确定了一个代表性实例的立体化学完整性。

  DOI：

  10.1039/b200163b
• 作为产物：
  描述：

  N-叔丁氧羰基-O-对甲苯磺酰基丝氨酸甲酯 在 碘 、 sodium iodide 、 锌 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 102.0h， 生成 methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2'-bromophenyl)propanoate
  参考文献：
  名称：

  SYNTHESIS OF N-(tert-BUTOXYCARBONYL)-a-IODOALANINE METHYL ESTER: A USEFUL BUILDING BLOCK IN THE SYNTHESIS OF NONNATURAL a-AMINO ACIDS VIA PALLADIUM CATALYZED CROSS COUPLING REACTIONS

  摘要：

  DOI：

  10.15227/orgsyn.081.0077

文献信息

• [EN] N-ACYL AMINO ACID COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS D'ACIDES AMINÉS N-ACYLE ET MÉTHODES D'UTILISATION
  申请人：PLIANT THERAPEUTICS INC

  公开号：WO2018049068A1

  公开（公告）日：2018-03-15

  The invention relates to compounds of formula (I), or a salt thereof wherein R1, A, L, and R2 and n are as described herein. Compounds of formula (I) and pharmaceutical compositions thereof are ανβ1 integrin inhibitors that are useful for treating tissue specific fibrosis.

  该发明涉及式(I)的化合物或其盐，其中R1、A、L、R2和n如本文所述。式(I)的化合物及其药物组成物是ανβ1整合素抑制剂，可用于治疗特定组织纤维化。
• N-acyl amino acid compounds and methods of use
  申请人：Pliant Therapeutics, Inc.

  公开号：US10604520B2

  公开（公告）日：2020-03-31

  The invention relates to compounds of formula (I): or a salt thereof, wherein R1, A, L, and R2 and n are as described herein. Compounds of formula (I) and pharmaceutical compositions thereof are αvβ1 integrin inhibitors that are useful for treating tissue specific fibrosis.

  本发明涉及式 (I) 化合物： 或其盐，其中 R1、A、L 和 R2 及 n 如本文所述。式（I）化合物及其药物组合物是αvβ1整合素抑制剂，可用于治疗组织特异性纤维化。
• Biaryl-Bridged Macrocyclic Peptides: Conformational Constraint via Carbogenic Fusion of Natural Amino Acid Side Chains
  作者：Falco-Magnus Meyer、James C. Collins、Brendan Borin、James Bradow、Spiros Liras、Chris Limberakis、Alan M. Mathiowetz、Laurence Philippe、David Price、Kun Song、Keith James

  DOI：10.1021/jo202105v

  日期：2012.4.6

  A general method for constraining peptide conformations via linkage of aromatic sidechains has been developed. Macrocydization of suitably functionalized tri-, tetra- and pentapeptides via Suzuki-Miyaura cross-coupling has been used to generate side chain to side chain, biaryl-bridged 14- to 21-membered macrocyclic peptides. Biaryl bridges possessing three different configurations, meta-meta, meta-ortho, and ortho-meta, were systematically explored through regiochemical variation of the aryl halide and aryl boronate coupling partners, allowing fine-tuning of the resultant macrocycle conformation. Suzuki-Miyaura macrocyclizations were successfully achieved both in solution and on solid phase for all three sizes of peptide. This approach constitutes a means of constraining peptide conformation via direct carbogenic fusion of side chains of naturally occurring amino acids such as phenylalanine and tyrosine, and so is complementary to strategies involving non-natural, for example, hydrocarbon, bridges.
• Thiol-based angiotensin-converting enzyme 2 inhibitors: P1′ modifications for the exploration of the S1′ subsite
  作者：David N. Deaton、Kevin P. Graham、Jeffrey W. Gross、Aaron B. Miller

  DOI：10.1016/j.bmcl.2008.01.046

  日期：2008.3

  Explorations of the S-1' subsite of ACE2 via modi. cations of the P-1' methylene biphenyl moiety of thiol-based metalloprotease inhibitors led to improvements in ACE2 selectivity versus ACE and NEP, while maintaining potent ACE2 inhibition. (C) 2008 Elsevier Ltd. All rights reserved.
• N-ACYL AMINO ACID COMPOUNDS AND METHODS OF USE
  申请人：Pliant Therapeutics, Inc.

  公开号：EP3509590A1

  公开（公告）日：2019-07-17