N-苄基-L-丙氨酸叔丁酯 | 85753-12-4

• 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
• 中文名称: N-苄基-L-丙氨酸叔丁酯
• 英文名称: N-benzyl-L-alanine tert-butyl ester
• 英文别名: N-benzyl-Ala-Ot-Bu；N-benzyl-L-alanine t-butyl ester；N-benzylalanine tert-butyl ester；tert-butyl (2S)-2-(benzylamino)propanoate
• CAS: 85753-12-4
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: ZACSMTDYVYATGT-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-苄基-L-丙氨酸叔丁酯 在 sodium hydride 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 28.75h， 生成 N-benzy-N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-alanine tert-butyl ester
  参考文献：
  名称：

  Selective Urokinase-Type Plasminogen Activator Inhibitors. 4. 1-(7-Sulfonamidoisoquinolinyl)guanidines

  摘要：

  1-isoquinolinylguanidines were previously disclosed as potent and selective inhibitors of urokinase-type plasminogen activator (uPA). Further investigation of this template has revealed that incorporation of a 7-sulfonamide group furnishes a new series of potent and highly selective uPA inhibitors. Potency and selectivity can be achieved with sulfonamides derived from a variety of amines and is further enhanced by the incorporation of sulfonamides derived from amino acids. The binding mode of these 1-isoquinolinylguanidines has been investigated by X-ray cocrystallization studies. uPA inhibitor 26 was selected for further evaluation based on its excellent enzyme potency (Ki 10 nM) and selectivity profile (4000-fold versus tPA and 2700-fold versus plasmin). In vitro, compound 26 is able to inhibit exogenous uPA in human chronic wound fluid (IC50=0.89 microM). In vivo, in a porcine acute excisional wound model, following topical delivery, compound 26 is able to penetrate into pig wounds and inhibit exogenous uPA activity with no adverse effect on wound healing parameters. On the basis of this profile, compound 26 (UK-371,804) was selected as a candidate for further preclinical evaluation for the treatment of chronic dermal ulcers.

  DOI：

  10.1021/jm061066t
• 作为产物：
  描述：

  L-丙氨酸叔丁酯盐酸盐 、 溴甲苯 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以95%的产率得到N-苄基-L-丙氨酸叔丁酯
  参考文献：
  名称：

  共定位策略在平滑受体的跨膜结构域中揭示了一个底面结合位点。

  摘要：

  我们通过共定位策略使用两个结构互补的光亲和探针，从已知的配体Allo-1衍生出了平滑受体（SMO）的底侧结合位点。对接研究和结构解剖确定了位点内的关键相互作用，包括氢键，π-π相互作用以及Allo-1及其接触残基之间的疏水相互作用。两者合计，我们的结果揭示了Allo-1结合的分子基础，并为克服药物耐药性的新一代配体的设计提供了基础。

  DOI：

  10.1021/acs.jmedchem.9b00283

文献信息

• Composition for the treatment of damaged tissue
  申请人：Pfizer Inc.

  公开号：US20030199440A1

  公开（公告）日：2003-10-23

  A pharmaceutical for use in damaged tissue, such as wound, treatment (e.g. healing) is described. The pharmaceutical comprising a composition which comprises: (a) a growth factor; and (b) an inhibitor agent; and optionally (c) a pharmaceutically acceptable carrier, diluent or excipient; wherein the inhibitor agent can inhibit the action of at least one specific adverse protein (e.g. a specific protease) that is upregulated in a damaged tissue, such as a wound, environment.

  描述了一种用于受损组织，如伤口治疗（例如愈合）的药物。该药物包括包含以下成分的组合物：（a）生长因子；和（b）抑制剂；以及可选的（c）药用载体、稀释剂或赋形剂；其中抑制剂可以抑制至少一种在受损组织，如伤口环境中上调的特定不良蛋白质（例如特定蛋白酶）的作用。
• Structure‐Activity Relationship Studies of Hydantoin‐Cored Ligands for Smoothened Receptor
  作者：Yang Liu、Fang Zhou、Kang Ding、Dongxiang Xue、Zhihao Zhu、Cuixia Li、Fei Li、Yueming Xu、Fei Xu、Zhiping Le、Suwen Zhao、Houchao Tao

  DOI：10.1002/open.202100216

  日期：2021.10

  A series of diaryl hydantoin analogs were synthesized and evaluated in the inhibition of Hedgehog pathway by targeting the smoothened receptor. Double halogen substituents introduced at two ends of the molecule greatly enhanced the potency.

  合成了一系列二芳基乙内酰脲类似物，并通过靶向平滑受体来评估其对 Hedgehog 通路的抑制作用。分子两端引入的双卤素取代基大大增强了效力。
• [EN] ABIRATERONE DERIVATIVES AND NON-COVALENT COMPLEXES WITH ALBUMIN<br/>[FR] DÉRIVÉS D'ABIRATÉRONE ET COMPLEXES NON COVALENTS AVEC L'ALBUMINE
  申请人：FL THERAPEUTICS LLC

  公开号：WO2015200837A1

  公开（公告）日：2015-12-30

  The present disclosure provides derivatives of abiraterone, non-covalently bound complexes of the abiraterone derivatives with serum albumin, pharmaceutical compositions of the same, and methods of use thereof. The non-covalently bound complexes are significantly more water-soluble than abiraterone and are useful for the treatment of a disease or condition that can benefit from CYP17 inhibition, such as prostate cancer.

  本公开提供了阿比特龙的衍生物，阿比特龙衍生物与血清白蛋白的非共价结合复合物，以及这些药物组合物的制备方法和使用方法。这些非共价结合复合物比阿比特龙具有更高的水溶性，可用于治疗需要CYP17抑制的疾病或病况，如前列腺癌。
• Entry to New Conformationally Constrained Amino Acids. First Synthesis of 3-Unsubstituted 4-Alkyl-4-carboxy-2-azetidinone Derivatives via an Intramolecular <i>N</i>^α<i>-C</i>^α-Cyclization Strategy
  作者：Guillermo Gerona-Navarro、Maria Angeles Bonache、Rosario Herranz、Maria Teresa García-López、Rosario González-Muñiz

  DOI：10.1021/jo015559b

  日期：2001.5.1

  N-benzyl-N-chloroacetyl amino acid derivatives is described. This study resulted in the first concise and versatile route to the preparation of 3-unsubstituted 4-alkyl-4-carboxy-2-azetidinones, to be included into the scarce family of beta-lactams with quaternary centers at the C(4) position. Particularly noteworthy is that the intramolecular N(alpha)-C(alpha)-cyclization of Phe and Leu derivatives afforded the

  描述了N-苄基-N-氯乙酰基氨基酸衍生物的碱基辅助分子内烷基化的系统研究。这项研究导致了第一个简洁而通用的制备3-未取代的4-烷基-4-羧基-2-氮杂环丁酮的方法，该方法将被包括在稀有的β-内酰胺类家族中，其四元中心在C（4）位置。特别值得注意的是，Phe和Leu衍生物的分子内Nα-Cα-环化作用提供了具有中等对映选择性（最高56％）的相应β-内酰胺衍生物。建议在这些特殊情况下，通过具有动态手性的平面烯醇中间体进行环化反应。所描述的反应顺序，与常用的α-羧基保护基团相容，
• N.sup.2 -alkoxynaphthalenesulfonyl-L-argininamides and the
  申请人：Mitsubishi Chemical Industries Limited

  公开号：US04046876A1

  公开（公告）日：1977-09-06

  N.sup.2 -alkoxynaphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis.

  N. sup. 2 -烷氧基萘磺酰-L-精氨酰胺及其药学上可接受的盐已被发现作为药物代理物，用于抑制和抑制血栓形成是有效的。