D,L-3-吲哚基甘氨酸甲酯 | 110317-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: D,L-3-吲哚基甘氨酸甲酯
• 英文名称: methyl 2-amino-2-(1H-indol-3-yl)acetate
• 英文别名: 2-(3-Indolyl)glycin-methylester；methyl indol-3-ylglycinate；amino-indol-3-yl-acetic acid methyl ester；Amino-indol-3-yl-essigsaeure-methylester
• CAS: 110317-48-1
• 化学式: C₁₁H₁₂N₂O₂
• mdl: MFCD01863401
• 分子量: 204.228
• InChiKey: BFIGWERHCJBNBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D,L-3-吲哚基甘氨酸甲酯 在 palladium on activated charcoal sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 环己烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 indol-3-yl-N-methyl-O-methoxyglycinamide
  参考文献：
  名称：

  Syntheses of Bis(3’-indolyl)-2(1H)-pyrazinones

  摘要：

  The syntheses of 3,6-bis(3'-indolyl)-2(1H)-pyrazinone and 3,5-bis(3'-indolyl)-2( 1H)-pyrazinone were described. Syntheses of 3,6-bis(3 '-indolyl)2(1H)-pyrazinone proceeded through the condensation of N-Boc-indolylglycine with indol-3-yl-N-methyl-O-methoxyglycinamide, and followed by reduction with LiAlH4 and cyclization of the resulting bisindolyl aldehyde-amine. 3,5-Bis(3'-indolyl)-2(1H)-pyrazinone was synthesized by cyclization of bisindolyl ketone amine in excess of ammonia under pressure.

  DOI：

  10.3987/com-00-8887
• 作为产物：
  描述：

  (Z)-2-(3-Indolyl)-2-(hydroxyimino)essigsaeure-methylester 在 Pd-BaSO₄ 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 3.0h， 以91%的产率得到D,L-3-吲哚基甘氨酸甲酯
  参考文献：
  名称：

  Droste, Holger; Wieland, Theodor, Liebigs Annalen der Chemie, 1987, p. 901 - 910

  摘要：

  DOI：

文献信息

• A practical approach to non-natural or N-unsubstituted α-arylglycine derivatives: Hf(OTf)4-doped Me3SiCl system-catalyzed aminomethylation of electron-rich arenes with a new type of N,O-acetal
  作者：Norio Sakai、Junichi Asano、Yuta Shimano、Takeo Konakahara

  DOI：10.1016/j.tet.2008.07.052

  日期：2008.9

  demonstrated the Hf(OTf)4-doped Me3SiCl system-catalyzed aminomethylation of electron-rich aromatic compounds, such as indoles and anilines, with new types of N,O-acetals having a variety of functional groups, such as cyano, ester, bis(trimethylsilyl)amino, diallylamino, and cyclic amino moieties, for the preparation of non-natural aromatic amino acid derivatives. Aminomethylation using an N,O-acetal with a

  作者已经证明了Hf（OTf）4掺杂的Me 3 SiCl系统催化的富电子芳族化合物（如吲哚和苯胺）的氨甲基化，以及具有各种官能团的新型N，O-乙缩醛，如氰基，酯，双（三甲基甲硅烷基）氨基，二烯丙基氨基和环状氨基部分，用于制备非天然芳香族氨基酸衍生物。在直接制备N-未取代的α-吲哚基甘氨酸衍生物的过程中，使用N，O-乙缩醛与双（三甲基甲硅烷基）氨基的氨基甲基化特别成功，该过程仅需进行标准的水性处理即可。
• In situ generation of 4π-sulphinylaminomethanide species from WXY–ZH systems and their cycloaddition reactions
  作者：Ronald Grigg、Marie Dowling、Visuvanathar Sridharan

  DOI：10.1039/c39860001777

  日期：——

  Sulphonyl group transfer from N-sulphonylaniline to α-amino acids and α-amino acids esters in solution at 25–110 °C gives rise to 4π-electron species believed to be sulphinylaminomethanide anions which can be trapped in good yield by N-substituted maleimides in 4π+ 2π cycloadditions.

  从磺酰基团转移Ñ -sulphonylaniline在溶液中α氨基酸和α氨基酸酯在25-110℃下引起4π电子物种被认为是能够以良好的收率被捕获由sulphinylaminomethanide阴离子Ñ -取代的马来酰亚胺在4π+2π环加成中
• Discovery of 5-((1H-indazol-3-yl) methylene)-2-thioxoimidazolidin-4-one derivatives as a new class of AHR agonists with anti-psoriasis activity in a mouse model
  作者：Guo Zhang、Ziyi Xia、Chenyu Tian、Anjie Xia、Jing You、Jie Liu、Shengyong Yang、Linli Li

  DOI：10.1016/j.bmcl.2023.129383

  日期：2023.8

  potential intervention target for psoriasis. Here, we report the discovery of 5-((1H-indazol-3-yl) methylene)-2-thioxoimidazolidin-4-one derivatives as a new class of AHR agonists. Structure-activity relationship analyses led to the identification of the most active compound, 5- ((1H-indazol-3-yl)methylene) -3- (prop-2-yn-1-yl) -2-thiooimidazolidin-4-one (24e), which exhibited an EC50 value of 0.015 µM

  芳烃受体（AHR）是一种配体依赖性转录因子，参与Th17/22和Treg细胞免疫平衡的调节。已发现它在皮肤中广泛表达，并参与银屑病的病理学。因此，AHR被认为是银屑病的潜在干预目标。在这里，我们报告发现了 5-((1 H -indazol-3-yl) mmethyl)-2-thioimidazolidin-4-one 衍生物作为一类新的 AHR 激动剂。构效关系分析确定了最活跃的化合物 5- ((1 H -indazol-3-yl)mmethyl) -3- (prop-2-yn-1-yl) -2-thiooimidazolidin-4 -one ( 24e )，其针对 AHR 的 EC 50值为 0.015 µM。作用机制研究表明24e通过激活AHR途径调节CYP1A1的表达。局部施用24e显着减轻了咪喹莫特(IMQ) 引起的银屑病样皮肤病变。总体而言，化合物24e可能是抗牛皮癣药物发现的
• A Novel Water-Soluble Gossypol Derivative Increases Chemotherapeutic Sensitivity and Promotes Growth Inhibition in Colon Cancer
  作者：Fei Yan、Xing-Xin Cao、Hai-Xia Jiang、Xiao-Long Zhao、Jian-Yong Wang、Yi-Hui Lin、Qiao-Ling Liu、Chen Zhang、Biao Jiang、Fang Guo

  DOI：10.1021/jm1001698

  日期：2010.8.12

  Compound 1 ((-)-gossypol) has been long known as a chemical anticancer agent. With its low water solubility and toxicity, it is not widely used as a commercial drug. To overcome these disadvantages, several novel derivatives of gossypol were designed, synthesized, and analyzed. One of the derivatives, compound 7 (6-aminopenicillanic acid sodium-gossypolone), was identified with great water solubility and anticancer property, suggested by inducing a dramatically decrease in Bcl-2 and Bcl-xL protein expression level found in vitro and growth inhibition of murine colon tumor in vivo. Furthermore, it was also recognized with less toxicity than compound 1 in vivo and significantly increased chemotherapeutic sensitivity against colon cancer in combination with traditional chemotherapeutic agent 5-fluorouracil. Therefore, it is concluded that compound 7 is superior to parent compound 1, and further preclinical studies of compound 7 is necessary for colon cancer therapy.
• 100. Syntheses in the indole series. Part I. Synthesis of indolyl-3-glyoxylic acid and of r-3-indolylglycine
  作者：John W. Baker

  DOI：10.1039/jr9400000458

  日期：——