D-phenylalanine tert-butyl ester | 6404-30-4

• 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
• 英文名称: D-phenylalanine tert-butyl ester
• 英文别名: t-butyl (R)-phenylalaninate；H-D-Phe-Ot-Bu；tert-butyl (2R)-2-amino-3-phenylpropanoate
• CAS: 6404-30-4
• 化学式: C₁₃H₁₉NO₂
• mdl: MFCD10001353
• 分子量: 221.299
• InChiKey: QOISWWBTZMFUEL-LLVKDONJSA-N

物化性质

• 沸点：
  303.3±22.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D-phenylalanine tert-butyl ester 在 palladium on activated charcoal N-甲基吗啉 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 N-[[4-(p-Toluoylamino)phenyl]sulfonyl]-D-phenylalanine t-butyl ester
  参考文献：
  名称：

  Highly Selective and Orally Active Inhibitors of Type IV Collagenase (MMP-9 and MMP-2):  N-Sulfonylamino Acid Derivatives

  摘要：

  Various N-sulfonylamino acid derivatives were synthesized and evaluated for their in vitro and in vivo activities to inhibit type IV collagenase (MMP-9 and MMP-2). When the amino acid residue and the sulfonamide moiety were modified, their inhibitory activities were greatly affected by the structure of the sulfonamide moiety. A series of aryl sulfonamide derivatives containing biaryl, tetrazole, amide, and triple bond were found to be potent and highly selective inhibitors of MMP-9 and MMP-2 In addition, these compounds were orally active in animal models of tumor growth and metastasis. These results revealed the potential of the N-sulfonylamino acid derivatives as a new type of candidate drug for the treatment of cancer.

  DOI：

  10.1021/jm9707582
• 作为产物：
  描述：

  D-苯丙氨酸 在 硫酸 、 10% palladium on activated carbon 、 氢气 、 sodium carbonate 、 magnesium sulfate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 28.0h， 生成 D-phenylalanine tert-butyl ester
  参考文献：
  名称：

  A Bismuth(III)-Catalyzed Friedel−Crafts Cyclization and Stereocontrolled Organocatalytic Approach to (−)-Platensimycin

  摘要：

  A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promotecl cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.

  DOI：

  10.1021/ol102390t

文献信息

• [EN] AZASULFURYLPEPTIDE-BASED CD36 MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS CD36 À BASE D'AZASULFURYLPEPTIDES ET UTILISATIONS DE CEUX-CI
  申请人：RSEM LTD PARTNERSHIP

  公开号：WO2016029324A1

  公开（公告）日：2016-03-03

  Novel azasulfuryl-containing peptidomimetics capable of inhibiting CD36 activity are disclosed. Use of these azasulfuryl-containing peptidomimetics for the treatment of CD36-related diseases, disorders or conditions, including TLR2-mediated inflammatory disease, disorder or condition, and methods of obtaining such azasulfuryl-containing peptidomimetics, are also disclosed.

  揭示了能够抑制CD36活性的新型含氮硫酰基的肽类模拟物。还揭示了利用这些含氮硫酰基的肽类模拟物治疗与CD36相关的疾病、紊乱或状况，包括TLR2介导的炎症性疾病、紊乱或状况的用途，以及获取这种含氮硫酰基的肽类模拟物的方法。
• [EN] DIPHENYLAZETIDINONE DERIVATES PROCESSING CHOLESTEROL ABSORPTION INHIBITORY ACTIVITY<br/>[FR] DERIVES DIPHENYLAZETIDINONE PRESENTANT UNE ACTIVITE D'INHIBITION D'ABSORPTION DU CHOLESTEROL
  申请人：ASTRAZENECA AB

  公开号：WO2005061451A1

  公开（公告）日：2005-07-07

  Compounds of formula (XV): [Chemical formula should be inserted here. Please see paper copy] (XV) (wherein variable groups are as defined within) pharmaceutically acceptable salts, solvates, solvates of such salts and prodrugs thereof and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia are described. Processes for their manufacture and pharmaceutical compositions containing them are also described.

  公式（XV）的化合物：[应在此处插入化学公式。请参见纸质副本]（XV）（其中变量组如内部定义）药物可接受的盐、溶剂化物、这些盐的溶剂化物和前药及其用作治疗高脂血症的胆固醇吸收抑制剂。还描述了它们的制造过程和含有它们的药物组合物。
• Influences of Histidine-1 and Azaphenylalanine-4 on the Affinity, Anti-inflammatory, and Antiangiogenic Activities of Azapeptide Cluster of Differentiation 36 Receptor Modulators
  作者：Kelvine Chignen Possi、Mukandila Mulumba、Samy Omri、Yesica Garcia-Ramos、Houda Tahiri、Sylvain Chemtob、Huy Ong、William D. Lubell

  DOI：10.1021/acs.jmedchem.7b01209

  日期：2017.11.22

  of the 1- and 4-position residues on the affinity, anti-inflammatory, and antiangiogenic activity of these azapeptides have now been studied in detail by the synthesis and analysis of a set of 25 analogues featuring Ala1 or His1 and a variety of aromatic side chains at the aza-amino acid residue in the 4-position. Although their binding affinities differed only by a factor of 17, the analogues exhibited

  生长激素释放肽6（GHRP-6）的Azapeptide类似物在分化36受体（CD36）的簇上显示出有希望的亲和力，选择性和调节剂活性。例如，先前显示[A 1，azaF 4 ]-和[azaY 4 ] -GHRP-6（1a和2b）与CD36选择性结合，并且在使用脉络膜外植体的微血管发芽试验中分别显示出显着的抗血管生成和轻微的血管生成活性。 。现在，通过合成和分析一组25个以Ala 1或His为特征的类似物，详细研究了1和4位残基对这些氮杂肽的亲和力，抗炎和抗血管生成活性的影响。1和在4-位的氮杂氨基酸残基处的各种芳族侧链。尽管它们的结合亲和力仅相差17倍，但这些类似物在巨噬细胞和脉络膜新生血管形成中调节一氧化氮（NO）产生的能力方面却表现出显着差异。
• Isopropenyl chlorocarbonate (IPCC)1 in amino acid and peptide chemistry: Esterification of N-protected amino acids; Application to the synthesis of the depsipeptide valinomycin
  作者：Choukri Zeggaf、Joël Poncet、Patrick Jouin、Marie-Noëlle Dufour、Bertrand Castro

  DOI：10.1016/s0040-4020(01)81083-8

  日期：1989.1

  Esterification of N-protected α-amino acids was achieved via isopropenyl chlorocarbonate (IPCC) activation. In situ alcoholysis of the unstable mixed anhydride intermediate was catalyzed by 4-(dimethylamino)pyridine (DMAP). Competing isopropenyl ester formation was negligible when using methylene chloride as the solvent. A variety of esters from primary and secondary alcohols were obtained with good

  N-保护的α-氨基酸的酯化反应是通过异丙烯基氯碳酸酯（IPCC）活化来实现的。不稳定的混合酸酐中间体的原位醇解反应是通过4-（二甲基氨基）吡啶（DMAP）催化的。当使用二氯甲烷作为溶剂时，竞争性异丙烯基酯的形成可忽略不计。从伯醇和仲醇获得的各种酯均具有良好的收率（60％至96％），即使在更剧烈的条件下，即使受阻更严重的叔丁醇也可提供可接受的收率。通过使用IPCC进行酯键形成，使用BOP试剂进行肽偶联和最后一步环化反应，制备抗生素瓦利霉素，可以说明depsipeptide合成方法的改进。
• Straightforward synthesis of enantiomerically pure 1,2,3-triazoles derived from amino esters
  作者：Gastón Silveira-Dorta、Sampad Jana、Lucie Borkova、Joice Thomas、Wim Dehaen

  DOI：10.1039/c8ob00533h

  日期：——

  A practical and straightforward approach that enables, for the first time, the synthesis of enantiomerically pure 1,4,5-trisubstituted, 1,5-disubstituted, and fused 1,2,3-triazole derivatives has been developed. The synthesis employs enantiomerically pure amino esters derived from amino acids and commercially available ketones under metal-free conditions.

  已经开发出一种实用且直接的方法，该方法首次能够合成对映体纯的1,4,5-三取代，1,5-二取代和稠合的1,2,3-三唑衍生物。该合成使用在无金属条件下衍生自氨基酸的对映体纯的氨基酯和可商购的酮。