(R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propionic acid

• 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
• 英文名称: (R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propionic acid
• 英文别名: phthaloyl-D-tryptophan；N-Phth-D-Trp-OH；D-RG108；RG108；(R)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(1H-indol-3-yl)-propionic acid；(2R)-2-(1,3-dioxoisoindol-2-yl)-3-(1H-indol-3-yl)propanoic acid
• 化学式: C₁₉H₁₄N₂O₄
• 分子量: 334.331
• InChiKey: HPTXLHAHLXOAKV-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  90.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propionic acid 在 2,6-二甲基吡啶 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.08h， 生成 N-Phth-D-Trp-Ala-OH
  参考文献：
  名称：

  Double Annulative Cascade of Tryptophan-Containing Peptides Triggered by Selectfluor

  摘要：

  A common dearomative strategy toward the kapakahines B/F and chaetominine natural products is reported. The proposed biomimetic strategy generates the tetracyclic alpha-carboline core in a single step, featuring a selectfluor-mediated dearomatization of preactivated N-Phth-Trp-Xaa-OR dipeptides at the C-terminus. The pivotal cascade includes a double annulation and the formation of three carbon-heteroatom bonds while gaining, for the first time, some insight on the diastereoselectivity outcome during the formation of the alpha-carboline fragment.

  DOI：

  10.1021/ol403281t
• 作为产物：
  描述：

  D-色氨酸 在 苯酐 、 盐酸 作用下， 以 吡啶 为溶剂， 反应 2.0h， 生成 (R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propionic acid
  参考文献：
  名称：

  皂苷的全合成。

  摘要：

  通过14个步骤有效地，不对称地合成了细胞毒性天然产物Chaetominine。该策略采用铜（I）介导的环化反应作为安装abc-三环系统的关键步骤，非对映选择性氧化和还原反应进一步完善了该系统。这项工作也证明了产生氧化性重排为同手性螺环吡咯烷二氯新吲哚的第一个例子。

  DOI：

  10.1021/ol802155n

文献信息

• Rapid Synthesis of New DNMT Inhibitors Derivatives of Procainamide
  作者：Ludovic Halby、Christine Champion、Catherine Sénamaud-Beaufort、Sophie Ajjan、Thierry Drujon、Arumugam Rajavelu、Alexandre Ceccaldi、Renata Jurkowska、Olivier Lequin、William G. Nelson、Alain Guy、Albert Jeltsch、Dominique Guianvarc'h、Clotilde Ferroud、Paola B. Arimondo

  DOI：10.1002/cbic.201100522

  日期：2012.1.2

  Rational inhibition: Conjugates of procainamide were produced by rapid synthetic pathways. Several compounds resulted in extremely potent inhibitors of the murine catalytic Dnmt3A/3L complex and of human DNMT1. The inhibition potency of procainamide conjugated to phtalimide depended on the length of the linker. Such conjugates also showed strong cytotoxicity against two tumour cell lines.

  合理的抑制作用：普鲁卡因酰胺的结合物是通过快速合成途径产生的。几种化合物产生了鼠催化Dnmt3A / 3L复合物和人DNMT1的极强抑制剂。与邻苯二甲酰亚胺偶联的普鲁卡因酰胺的抑制能力取决于接头的长度。此类缀合物还显示出对两种肿瘤细胞系的强细胞毒性。
• Second-Generation, Biomimetic Total Synthesis of Chaetominine
  作者：Gwilherm Evano、Alexis Coste、Ganesan Karthikeyan、François Couty

  DOI：10.1055/s-0029-1216923

  日期：2009.9

  A straightforward total synthesis of the potent anticancer agent (-)-chaetominine is reported. Central to this synthesis was a biomimetic oxidative cyclization of a tryptophanyl-alanine dipeptide, which provided a fully elaborated 1,2,3,4-tetrahydropyrido[2,3-b]indole. Reduction of this intermediate followed by spontaneous cyclization and installation of the side chain provided synthetic chaetominine

  报道了有效的抗癌药（-）-chaetominine的直接全合成。该合成的中心是色氨酸-丙氨酸二肽的仿生氧化环化，其提供了充分加工的1,2,3,4-四氢吡啶并[2,3- b ]吲哚。还原该中间体，然后自发环化并安装侧链，从商业上可得的廉价起始原料开始，以九个步骤的顺序以9％的总收率提供了合成的树脂胺。 生物碱-全合成-氧化环化-抗癌剂-肽
• Generating hepatocytes
  申请人：The J. David Gladstone Institutes, a testamentary trust established under the Will of J. David Gladstone

  公开号：US10227565B2

  公开（公告）日：2019-03-12

  Compositions and methods are described herein for inducing reprogramming of non-pluripotent cells across lineage and differentiation boundaries to generate endodermal progenitor cells and hepatocytes. Compositions and methods for expansion of endodermal progenitor cells without loss of phenotype are also described herein.

  本文描述了诱导非多能细胞跨系和分化边界重编程以产生内胚层祖细胞和肝细胞的组合物和方法。本文还描述了在不丧失表型的情况下扩增内胚层祖细胞的组合物和方法。
• Methods and compositions for producing pancreatic beta cells
  申请人：The Regents of the University of California

  公开号：US11332716B2

  公开（公告）日：2022-05-17

  Compositions and methods of producing mammalian cell populations that include a high proportion of pancreatic beta cells are described herein. Such cell populations are useful for treatment of diabetes. Also provided are materials and methods for the direct differentiation of stem cells, such as embryonic stem cells, into functional pancreatic beta cells. The disclosure provides the benefit of direct differentiation, which results in the production of functional pancreatic beta cells efficiently and at low cost.

  本文描述了生产包括高比例胰腺β细胞的哺乳动物细胞群的组合物和方法。这种细胞群可用于治疗糖尿病。还提供了将胚胎干细胞等干细胞直接分化为功能性胰腺β细胞的材料和方法。本公开内容提供了直接分化的好处，可高效低成本地生产功能性胰腺β细胞。
• Cyclomaltooligosaccharide-assisted spectroscopic discrimination of phthalimido-derived amino acids through the formation of molecular aggregates
  作者：Branko S. Jursic、Paresh K. Patel

  DOI：10.1016/j.carres.2006.09.013

  日期：2006.12

  Spectroscopic evidence was used to demonstrate the formation of molecular associates in an aqueous solution of phthalimido tryptophan. These molecular associates are loosely formed through 7r-n aromatic stacking, properties that are not sufficient to cause NMR spectroscopic enantiomeric discrimination. A cyclomaltooligosaccharide with a larger cavity, such as cyclomaltooctaose (gamma-cyclodextrin), is capable of forming a ternary complex with these molecular associates and enhances pi-pi aromatic stacking interactions, resulting in NMR enantiomeric discrimination. Electrospray-ionization mass spectroscopy (ESIMS) and NOESY two-dimensional NMR spectroscopic methods were used to study these complexes. Association constants and thermodynamic data for these cyclomaltooligosaccharide complexes were also estimated. (c) 2006 Elsevier Ltd. All rights reserved.