(R)-(1-(4-甲氧基苯基)-3-氧代丙-2-基)氨基甲酸叔丁酯 | 120349-76-0

• 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: (R)-(1-(4-甲氧基苯基)-3-氧代丙-2-基)氨基甲酸叔丁酯
• 英文名称: Carbamic acid, [1-formyl-2-(4-methoxyphenyl)ethyl]-, 1,1-dimethylethyl ester, (R)-
• 英文别名: tert-butyl N-[(2R)-1-(4-methoxyphenyl)-3-oxopropan-2-yl]carbamate
• CAS: 120349-76-0
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: RSVZHGTYMCODNB-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 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：

  (R)-(1-(4-甲氧基苯基)-3-氧代丙-2-基)氨基甲酸叔丁酯 在 potassium osmate(VI) 、 AD-mix-α 、 Hydroquinone 1,4-phthalazinediyl diether 作用下， 以 叔丁醇 、 苯 为溶剂， 反应 33.0h， 生成 ethyl (2R,3S,4R)-4-(tert-butoxycarbonyl)amino-2,3-dihydroxy-5-(4-methoxyphenyl)pentanoate
  参考文献：
  名称：

  以d-酪氨酸为原料高效合成(-)-脱乙酰茴香霉素

  摘要：

  以 Sharpless 不对称二羟基化为关键反应，从 D-酪氨酸开始合成抗生素 (-)-去乙酰茴香霉素。

  DOI：

  10.1055/s-2002-33904
• 作为产物：
  描述：

  methyl (R)-2-amino-3-(4-methoxyphenyl)propanoate 在 sodium tetrahydroborate 、 草酰氯 、 sodium carbonate 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 生成 (R)-(1-(4-甲氧基苯基)-3-氧代丙-2-基)氨基甲酸叔丁酯
  参考文献：
  名称：

  从D-酪氨酸或L-酪氨酸开始的（-）-茴香霉素或（+）-茴香霉素的新合成

  摘要：

  （R）-2-（对甲氧基苯基）甲基-2,5-二氢吡咯（-）-及其（S）-异构体（+）- ，（-）-阿霉素（-）-和（+）的手性中间体-anisomycin（+）-分别通过D-酪氨酸和L-酪氨酸分别通过顺式-烯化步骤有效合成。

  DOI：

  10.1016/s0040-4039(00)80511-0

文献信息

• [EN] HETEROCYCLIC DERIVATIVES AND THEIR USE AS ANTITHROMBOTIC AGENTS<br/>[FR] DERIVES HETEROCYCLIQUES ET LEUR UTILISATION EN TANT QU'AGENTS ANTITHROMBOTIQUES
  申请人：AKZO NOBEL N.V.

  公开号：WO1998047876A1

  公开（公告）日：1998-10-29

  (EN) The present invention relates to antithrombotic compounds comprising the group Q, Q having formula (I), wherein the substructure (i) is a structure selected from (a, b and c), wherein X is O or S; X' being independently CH or N; and m is 0, 1, 2 or 3; wherein the group Q is bound through an oxygen atom or an optionally substituted nitrogen or carbon atom, or a pharmaceutically acceptable salt thereof or a prodrug thereof. The compounds of the invention are therapeutically active and in particular are antithrombotic agents.(FR) La présente invention concerne des composé antithrombotiques comprenant le groupe Q correspondant à la formule (I) dans laquelle la sous-structure (i) est une structure choisie parmi (a), (b) ou (c) où X représente O ou S, X' représente indépendamment CH ou N, et m vaut 0, 1, 2 ou 3, le groupe Q étant fixé au moyen d'un atome d'oxygène ou d'un atome de carbone ou d'azote éventuellement substitué. L'invention concerne également un sel ou un promédicament de ces composés, acceptable sur le plan pharmacologique. Les compositions de l'invention sont actives sur le plan thérapeutique et constituent notamment des agents antithrombotiques.

  该发明涉及抗血栓化合物，包括具有公式（I）的Q基团，其中亚结构（i）是从（a）、（b）和（c）中选择的结构，其中X为O或S；X'独立地为CH或N；m为0、1、2或3；其中Q基团通过氧原子或可选择的取代氮或碳原子结合，或其药学可接受的盐或前药。该发明的化合物具有治疗活性，特别是抗血栓剂。
• Synthesis of New (−)-Bestatin-Based Inhibitor Libraries Reveals a Novel Binding Mode in the S1 Pocket of the Essential Malaria M1 Metalloaminopeptidase
  作者：Geetha Velmourougane、Michael B. Harbut、Seema Dalal、Sheena McGowan、Christine A. Oellig、Nataline Meinhardt、James C. Whisstock、Michael Klemba、Doron C. Greenbaum

  DOI：10.1021/jm101227t

  日期：2011.3.24

  The malarial PfA-M1 metalloaminopeptidase is considered a putative drug target. The natural product dipeptide mimetic, bestatin, is a potent inhibitor of PfA-M1. Herein we present a new, efficient, and high-yielding protocol for the synthesis of bestatin derivatives from natural and unnatural N-Boc-D-amino acids. A diverse library of bestatin derivatives was synthesized with variants at the side chain of either the alpha-hydroxy-beta-amino acid (P1) or the adjacent natural a-amino add (P1'). Surprisingly, we found that extended aromatic side chains at the P1 position resulted in potent inhibition against PfA-M1. To understand these data, we determined the X-ray cocrystal structures of PfA-M1 with two derivatives having either a Tyr(OMe) 15 or Tyr(OBz1) 16 at the 131 position and observed substantial inhibitor-induced rearrangement of the primary loop within the PEA-M1 pocket that interacts with the PI side chain. Our data provide important insights for the rational design of more potent and selective inhibitors of this enzyme that may eventually lead to new therapies for malaria.
• Structure–Activity Relationship Study of a CXC Chemokine Receptor Type 4 Antagonist, FC131, Using a Series of Alkene Dipeptide Isosteres
  作者：Kazuya Kobayashi、Shinya Oishi、Ryoko Hayashi、Kenji Tomita、Tatsuhiko Kubo、Noriko Tanahara、Hiroaki Ohno、Yasushi Yoshikawa、Toshio Furuya、Masaru Hoshino、Nobutaka Fujii

  DOI：10.1021/jm2016914

  日期：2012.3.22

  A structure-activity relationship study on a highly potent CXC chemokine receptor type 4 (CXCR4) antagonist, FC131 [cyclo(-D-Tyr(1)-Arg(2)-Arg(3)-Nal(4)-Gly(5)-)], was carried out using a series of alkene isosteres of the D-Tyr(1)-L/D-Arg(2) dipeptide to investigate the binding mode of FC131 and its derivatives with CXCR4. The structure-activity relationships of isostere-containing FC131 analogues were similar to those of the parent FC131 and its derivatives, suggesting that a trans-conformer of the D-Tyt(1)-Arg(2) peptide bond is the dominant contributor to the bioactive conformations of FC131. Although NMR analysis demonstrated that the two conformations of the peptidomimetic containing the D-Tyr(1)-D-Arg(2) isostere are possible, binding-mode prediction indicated that the orientations of the alkene motif within D-Tyr(1)-MeArg(2) peptidomimetics depend on the chirality of Arg(2) and the beta-methyl group of the isostere unit, which makes the dominant contribution for binding to the receptor. The most potent FC122 [cyclo(-D-Tyr(1)-D-MeArg(2)-Arg(3)-Nal(4)-Gly(5)-)] bound with CXCR4 by a binding mode different from that of FC131.
• JEGHAM, SAMIR;DAS, BHUPESH C., TETRAHEDRON LETT., 29,(1988) N 35, C. 4419-4422
  作者：JEGHAM, SAMIR、DAS, BHUPESH C.

  DOI：——

  日期：——
• HETEROCYCLIC DERIVATIVES AND THEIR USE AS ANTITHROMBOTIC AGENTS
  申请人：Akzo Nobel N.V.

  公开号：EP0975600A1

  公开（公告）日：2000-02-02