N-吲哚-3-基乙酰基-色氨酸 | 57105-53-0

• 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
• 中文名称: N-吲哚-3-基乙酰基-色氨酸
• 英文名称: (S)-N-(1H-indole-3-acetyl)tryptophan
• 英文别名: (2S)-3-(1H-indol-3-yl)-2-[(1H-indol-3-ylacetyl)amino]propanoic acid；IAA-L-Trp-OH；(S)-2-(2-(1H-indol-3-yl)acetamido)-3-(1H-indol-3-yl)propanoic acid；N^α-indol-3-ylacetyl-L-tryptophan；INDOLE-3-ACETYL-DL-TRYPTOPHAN；(2S)-3-(1H-indol-3-yl)-2-[[2-(1H-indol-3-yl)acetyl]amino]propanoic acid
• CAS: 57105-53-0
• 化学式: C₂₁H₁₉N₃O₃
• 分子量: 361.4
• InChiKey: FOSPCYZZRVNHJS-IBGZPJMESA-N

物化性质

• 熔点：
  181-183 °C
• 沸点：
  767.2±60.0 °C(Predicted)
• 密度：
  1.399±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 室温 |

反应信息

• 作为反应物：
  描述：

  3-[[(2S)-6-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoyl]-[(1S)-1-phenylethyl]amino]propanoic acid 、 N-吲哚-3-基乙酰基-色氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  端基修饰：一种有效的工具，可提高抗菌肽类似物对革兰氏阳性细菌的活性。

  摘要：

  耐多药细菌菌株感染的发生率增加，因此有必要对新的潜在抗菌剂进行深入研究。在这里，经过优化的阳离子/疏水交替设计的抗菌肽类似物仅对革兰氏阳性病原体具有中等活性。通常，在N端引入疏水部分导致类似物具有明显增强的抗多药性金黄色葡萄球菌和粪肠球菌的活性。有趣的是，抗大肠杆菌菌株的效力不受影响，而疏水部分的修饰导致对革兰氏阴性鲍曼不动杆菌的活性增加。尽管对鼠成纤维细胞和人脐静脉内皮细胞的细胞毒性增加，优化的肽类似物表现出显着改善的细胞选择性。总的来说，发现最有利的疏水活性诱导部分是环己基乙酰基和五氟苯基乙酰基，而短的PEG样链的存在对活性没有显着影响。阳离子部分的引入对类似物没有作用，或仅赋予中等程度的促进活性的作用。

  DOI：

  10.1016/j.ejpb.2015.01.013
• 作为产物：
  描述：

  methyl (2S)-3-(1H-indol-3-yl)-2-[(1H-indol-3-ylacetyl)amino]propanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以95%的产率得到N-吲哚-3-基乙酰基-色氨酸
  参考文献：
  名称：

  合成生长素-氨基酸缀合物的制备

  摘要：

  摘要 生长素酰胺结合物是最重要的生长素、吲哚-3-乙酸 (IAA) 的调节剂，IAA 被认为负责植物内的许多重要过程。在此，IAA 的酰胺缀合物在 1-羟基苯并三唑的存在下，采用一种简单有效的偶联方法与 WSCI·HCl（一种水溶性缩合剂）合成。具有 10 个氨基酸的 IAA 缀合物及其相应的甲酯以优异的产率制备，高达 95%，旨在促进它们在植物物种中的鉴定。八种 IAA-氨基酸甲酯结合物首次在此得到表征。图形概要

  DOI：

  10.1080/00397911.2019.1605446

文献信息

• PESTICIDAL COMPOSITION COMPRISING INDOLE DERIVATES
  申请人：Bednarek Pawel

  公开号：US20090028796A1

  公开（公告）日：2009-01-29

  The present invention is directed to pesticidal compositions comprising indole derivatives. These indole derivatives are especially active against phytopathogenic fungi. Furthermore, the invention relates to the use of indole derivatives for the production of pesticides and the use of the compositions according to the invention as pesticides. The present invention is also directed to a process for producing a pesticidal composition and to pesticidal compositions prepared by this process. In addition, the invention relates to a process for preventing or combating pests and to a process for protecting plants against pests, especially against phytopathogenic fungi. Further, the invention is directed to plants or seeds as well as objects or materials which have been protected against pests by treatment with a composition according to the invention. Further, the invention is directed to a method for identifying a substance having pesticidal activity. Further, the invention is directed to a method of identifying the mode of action of and/or of providing binding proteins for a pesticidal compound of the present invention. Finally, the invention is directed to a method for diagnosing pest infection of a plant and to the use of a pesticidal compound of the present invention as diagnostic markers.

  本发明涉及包含吲哚衍生物的杀虫组合物。这些吲哚衍生物特别对植物病原真菌具有活性。此外，本发明涉及使用吲哚衍生物制备杀虫剂以及使用本发明中的组合物作为杀虫剂。本发明还涉及制备杀虫组合物的过程以及通过该过程制备的杀虫组合物。此外，本发明还涉及预防或对抗害虫的过程以及保护植物免受害虫，特别是植物病原真菌的过程。此外，本发明还涉及经过本发明中的组合物处理后受到保护的植物或种子以及物体或材料。本发明还涉及识别具有杀虫活性的物质的方法。此外，本发明还涉及识别本发明中杀虫化合物的作用方式和/或提供结合蛋白的方法。最后，本发明涉及诊断植物害虫感染的方法以及使用本发明中的杀虫化合物作为诊断标记的方法。
• Estolides of vegetable oil alkoxylates and method of making and using
  申请人：Indorama Ventures Oxides LLC

  公开号：US11136528B2

  公开（公告）日：2021-10-05

  A method of reacting castor oil and an alkoxylated glycerin via a transesterification reaction to produce an estolide of castor oil alkoxylate. Compositions comprising an estolide of castor oil alkoxylate and uses thereof.

  一种通过酯交换反应使蓖麻油和烷氧基化甘油反应生成蓖麻油烷氧基化酯的方法。包含蓖麻油烷氧基化酯的组合物及其用途。
• Syntheses of IAA- and IPA-Amino Acid Conjugates
  作者：Alan R. Katritzky、Levan Khelashvili、Munawar Ali Munawar

  DOI：10.1021/jo8017796

  日期：2008.11.21

  Amino acid derivatives of IAA and IPA are prepared conveniently and efficiently by coupling of readily available 2a-b with diverse free amino acids 3a-g and (3c+3c') to give compounds 4a-j, (4c+4c') and (4h+4h') in 38-70% yields. Similarly, 2a-b afforded IAA and IPA peptide conjugates 6a-b in 32-40% yields. Complete retention of chirality was supported by NMR and HPLC analysis.
• Notes - Synthesis of 3-Indoleacetamides
  作者：Lowell Weller、Harold Sell

  DOI：10.1021/jo01105a602

  日期：1958.11
• Tryptophan and thiosemicarbazide derivatives: design, synthesis, and biological evaluation as potential β-d-galactosidase and β-d-glucosidase inhibitors
  作者：Reema Abu Khalaf、Ahmed Mutanabbi Abdula、Mohammad S. Mubarak、Mutasem O. Taha

  DOI：10.1007/s00044-014-1314-4

  日期：2015.6

  Glycosidases, including beta-d-galactosidase and beta-d-glucosidase, are involved in a range of metabolic disorders, such as cancer, viral or bacterial infections, and diabetes. Previously, we scanned the pharmacophoric space of these enzymes and had a self-consistent and predictive quantitative structure-activity relationship that was used to identify several beta-d-galactosidase and beta-d-glucosidase inhibitors via in silico search of structural databases. Guided by the preceding modeling efforts, synthesis of a series of tryptophan and thiosemicarbazide derivatives as beta-d-galactosidase and beta-d-glucosidase inhibitors that match the generated pharmacophores followed by in vitro bioassay was carried out. Synthesized compounds 3c (37 % inhibition at 100 A mu M) and 4d (49 % inhibition at 100 A mu M) exhibited the best inhibitory bioactivities against beta-d-galactosidase and beta-d-glucosidase, respectively. They can serve as a promising lead compounds for the development of potential glycosidase inhibitors.