L-tryptophan methyl ester hydrochloride | 5619-09-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 色氨酸类衍生物
• 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: L-tryptophan methyl ester hydrochloride
• 英文别名: methyl L-tryptophanate hydrochloride；methyl L-tryptophanate monohydrochloride；[3-(1H-indol-3-yl)-1-methoxy-1-oxopropan-2-yl]azanium;chloride
• CAS: 5619-09-0
• 化学式: C₁₂H₁₄N₂O₂*ClH
• 分子量: 254.716
• InChiKey: XNFNGGQRDXFYMM-UHFFFAOYSA-N

物化性质

• 熔点：
  221-222
• 溶解度：
  溶于甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn,Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  L-tryptophan methyl ester hydrochloride 在 对甲苯磺酸 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 70.0h， 生成 9H-吡啶并[3,4-b]吲哚-3-羧酸
  参考文献：
  名称：

  Maclaren, John A., Australian Journal of Chemistry, 1989, vol. 42, # 6, p. 813 - 821

  摘要：

  DOI：

文献信息

• Design and Synthesis of Novel Xyloketal Derivatives and Their Protective Activities against H2O2-Induced HUVEC Injury
  作者：Shixin Liu、Rong Luo、Qi Xiang、Xianfang Xu、Liqin Qiu、Jiyan Pang

  DOI：10.3390/md13020948

  日期：——

  In this work, we designed and synthesized a series of amide derivatives (1–13), benzoxazine derivatives (16–28) and amino derivatives (29–30) from xyloketal B. All 28 new derivatives and seven known compounds (14, 15, 31–35) were evaluated for their protection against H2O2-induced HUVEC injury. 23 and 24 exhibited more potential protective activities than other derivatives; and the EC50 values of them and the leading compound 31 (xyloketal B) were 5.10, 3.59 and 15.97 μM, respectively. Meanwhile, a comparative molecular similarity indices analysis (CoMSIA) was constructed to explain the structural activity relationship of these xyloketal derivatives. This 3D QSAR model from CoMSIA suggested that the derived model exhibited good predictive ability in the external test-set validation. Derivative 24 fit well with the COMSIA map, therefore it possessed the highest activity of all compounds. Compounds 23, 24 and 31 (xyloketal B) were further to examine in the JC-1 mitochondrial membrane potential (MMP) assay of HUVECs using flow cytometry (FCM). The result indicated that 23 and 24 significantly inhibited H2O2-induced decrease of the cell mitochondrial membrane potential (ΔΨm) at 25 μM. Collectively, the protective effects of xyloketals on H2O2-induced endothelial cells may be generated from oxidation action by restraining ROS and reducing the MMP.

  在这项工作中，我们设计并合成了从木梨甲酯B出发的一系列酰胺衍生物（1-13）、苯并恶嗪衍生物（16-28）和氨基衍生物（29-30）。所有28个新衍生物和七个已知化合物（14，15，31-35）都被评估了它们对H2O2诱导的HUVEC损伤的保护作用。23和24表现出比其他衍生物更高的保护活性；它们的EC50值分别为5.10、3.59和15.97μM。同时，我们构建了一个比较分子相似性指数分析（CoMSIA）来解释这些木梨甲酯衍生物的结构活性关系。这个3D QSAR模型来自CoMSIA，表明推导出的模型在外部测试集验证中显示出良好的预测能力。衍生物24很好地符合CoMSIA图，因此它的活性最高。化合物23、24和31（木梨甲酯B）进一步在JC-1线粒体膜电位（MMP）分析中使用流式细胞术（FCM）对HUVECs进行检测。结果表明，23和24在25μM下显著抑制了H2O2诱导的细胞线粒体膜电位（ΔΨm）的降低。总体而言，木梨甲酯对H2O2诱导的血管内皮细胞的保护作用可能来自通过抑制ROS和减少MMP的氧化作用。
• Studies towards the synthesis of diazonamide A. Synthesis of the indole bis-oxazole fragment
  作者：Mark C Bagley、S.Lucy Hind、Christopher J Moody

  DOI：10.1016/s0040-4039(00)01120-5

  日期：2000.8

  The indole bis-oxazole 2, a potential intermediate for the synthesis of the marine natural product diazonamide A 1, has been synthesised, and attempts to construct the model macrocycle (ring B) 3 are also described; in both approaches rhodium carbenoid N–H insertion reactions are used in key steps.

  已经合成了吲哚双恶唑2（一种潜在的合成海洋天然产物重氮酰胺A 1的中间体），并描述了构建模型大环（环B）3的尝试。在这两种方法中，关键步骤均使用铑类胡萝卜素N–H插入反应。
• Na₂S₂O₈-mediated efficient synthesis of isothiocyanates from primary amines in water
  作者：Zhicheng Fu、Wenhao Yuan、Ning Chen、Zhanhui Yang、Jiaxi Xu

  DOI：10.1039/c8gc02261e

  日期：——

  We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates

  我们已经开发了两种绿色，实用且有效的方法，包括一锅法，可通过胺和二硫化碳通过胺合成异硫氰酸酯。用过硫酸钠脱硫。使用水作为溶剂。为了使异硫氰酸酯具有良好的化学选择性，必须具备碱性条件。通过两种方法，结构令人满意的直链和支链烷基胺和芳基胺很容易以令人满意的产率转化为异硫氰酸酯。卤素，苄基CH键，甲硫基，硝基，酯，烯基，富电子或不足的（杂）芳基，乙炔基，甚至酚和醇羟基均被很好地耐受。在水中一锅法也可用于从手性胺制备手性异硫氰酸酯，以及用游离氨基修饰生物活性结构。在大规模制备中，开发了独立于柱色谱法的简单实用的纯化方法。
• [EN] PYRIMIDYL CYCLOPENTANES AS AKT PROTEIN KINASE INHIBITORS<br/>[FR] PYRIMIDYL CYCLOPENTANES EN TANT QU'INHIBITEURS DE PROTÉINE KINASE AKT
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2009089454A1

  公开（公告）日：2009-07-16

  The present invention provides compounds of Formula (I) including tautomers, resolved enantiomers, resolved diastereomers, solvates, metabolites, salts and pharmaceutically acceptable prodrugs thereof. Also provided are methods of using the compounds of this invention as Akt protein kinase inhibitors and for the treatment of Akt-mediated diseases, for example, hyperproliferative diseases such as cancer.

  本发明提供了式（I）的化合物，包括互变异构体、已分离的对映体、已分离的非对映异构体、溶剂合物、代谢物、盐以及其药学上可接受的前药。本发明还提供了使用这些化合物作为Akt蛋白激酶抑制剂以及用于治疗Akt介导的疾病，例如，高增殖性疾病如癌症的方法。
• Novel <i>N</i>-transfer reagent for converting α-amino acid derivatives to α-diazo compounds
  作者：Guan-Han Lu、Tzu-Chia Huang、Hsiao-Chin Hsueh、Shin-Cherng Yang、Ting-Wei Cho、Ho-Hsuan Chou

  DOI：10.1039/d1cc01285a

  日期：——

  direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides from N-terminal dipeptides (32 examples, up to 91%)

  开发了一种新型通用N-转移试剂，可在温和的碱性条件下直接有效地将 α-氨基酮、乙酰胺和酯转化为相应的 α-重氮产物。这种一步合成方法不仅允许从 α-氨基酸衍生物生成 α-取代-α-重氮羰基化合物，而且允许从N-末端二肽制备 α-重氮二肽（32 个例子，高达 91%） .