N^α-acetyl-5-chloro-D,L-tryptophan | 114872-68-3

• 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: N^α-acetyl-5-chloro-D,L-tryptophan
• 英文别名: Ac-5'-Cl-Trp-OH；N-acetyl-5-chloro-DL-Trp；2-acetamido-3-(5-chloro-1H-indol-3-yl)propanoic acid
• CAS: 114872-68-3
• 化学式: C₁₃H₁₃ClN₂O₃
• 分子量: 280.711
• InChiKey: AXNQXTDSDFQIJV-UHFFFAOYSA-N

物化性质

• 沸点：
  610.6±55.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N^α-acetyl-5-chloro-D,L-tryptophan 在 4-二甲氨基吡啶 、 乙酸酐 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of novel tryptoline derivatives as indoleamine 2,3-dioxygenase (IDO) inhibitors

  摘要：

  Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against IDO. Substituted tryptoline derivatives (11a, 11c, 11e, 12b and 12c) were demonstrated to be more potent than known inhibitor MTH-Trp. Suzuki-Miyaura cross-coupling reaction of 11a-d with phenylboronic acid proceeded in high yields. In most cases, C5 and C6 substitutions on the corresponding indole ring were well tolerated. The tryptoline derivative 11c is a promising chemical lead for the discovery of novel IDO inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.028
• 作为产物：
  描述：

  acetylamino-(5-chloro-indol-3-ylmethyl)-malonic acid diethyl ester 、 sodium hydroxide 以87%的产率得到
  参考文献：
  名称：

  PORTER, JOHN;DYKERT, JOHN;RIVIER, JEAN, INT. J. PEPTIDE AND PROTEIN RES., 30,(1987) N 1, 13-21

  摘要：

  DOI：

文献信息

• A fast and direct iodide-catalyzed oxidative 2-selenylation of tryptophan
  作者：Yu-Ting Gao、Shao-Dong Liu、Liang Cheng、Li Liu

  DOI：10.1039/d1cc00700a

  日期：——

  We have developed a novel methodology for the synthesis of valuable 2-selenylated tryptophans from diselenides under the catalysis of iodide.

  我们已经开发出一种新颖的方法，可以在碘化物的催化下，从二硒化物合成具有价值的2-硒基色氨酸。
• The facile synthesis of a series of tryptophan derivatives
  作者：Georg Blaser、John M. Sanderson、Andrei S. Batsanov、Judith A.K. Howard

  DOI：10.1016/j.tetlet.2008.02.120

  日期：2008.4

  of 5- and 6-substituted tryptophan derivatives that are difficult to prepare using alternative enzymatic approaches. Acylation of an activated amino acid, derived from serine in situ, is coupled with an enzymatic resolution step to furnish enantiopure analogues bearing a range of electron withdrawing and releasing substituents. Isolation of a dehydroalanine derivative as a by-product from some reactions

  这项研究报告了一种简便的方法，用于合成各种5和6取代的色氨酸衍生物，这些色素很难使用替代酶方法制备。原位衍生自丝氨酸的活化氨基酸的酰化与酶促拆分步骤相结合，以提供带有一系列吸电​​子和释放电子的取代基的对映纯类似物。从某些反应中分离出作为副产物的脱氢丙氨酸衍生物，可为该反应的可能机理提供一些见解。
• Tryptophan derivatives regulate the seed germination and radicle growth of a root parasitic plant, Orobanche minor
  作者：Michio Kuruma、Taiki Suzuki、Yoshiya Seto

  DOI：10.1016/j.bmcl.2021.128085

  日期：2021.7

  post-radicle growth of O. minor. We designed a hybrid chemical (13), in which IAA is attached to a part of SL, and found that this synthetic analog induced the germination of O. minor, and also inhibited post-radicle growth. Moreover, contrary to our expectations, we found that N-acetyl Trp (9) showed germination stimulating activity, and introduction of a substitution at C-5 position increased its activity

  根寄生植物萌发由宿主衍生的化学物质独脚金内酯 (SL) 诱导。我们发现主要的微生物培养液成分胰蛋白胨抑制根寄生植物Orobanche minor的 SL 诱导萌发。从色氨酸中分离出作为活性化合物的l -色氨酸 ( l -Trp)。我们进一步发现l- Trp 相关化合物 ( 1b - 11 )，如主要的植物激素生长素 ( 8，indole-3-乙酸；IAA)，也抑制O. minor的萌发和胚根后生长。我们设计了一种混合化学品（13)，其中 IAA 连接到 SL 的一部分，并发现这种合成类似物诱导了O. minor的萌发，也抑制了胚根后的生长。此外，与我们的预期相反，我们发现N-乙酰 Trp ( 9 ) 显示出萌发刺激活性，并且在 C-5 位置引入取代增加了其活性 ( 12a - 12f )。我们的数据，特别是发现具有两种活性的结构杂化化合物，可诱导自发发芽和抑制随后的自由基生长，将为根寄生植物提供新型发芽调节剂。
• Total synthesis and antibacterial evaluation of nicrophorusamides A and B
  作者：Yuto Katayama、Yudai Nishikawa、Minoru Inagaki、Jiyoon Park、Dong-Chan Oh、Yuichi Masuda

  DOI：10.1016/j.tetlet.2024.155177

  日期：2024.7

  This paper reports the total synthesis of antibacterial cyclic hexapeptides nicrophorusamides A () and B (), isolated from the actinomycete strain UTG9 belonging to the genus . The synthesis involved solid-phase peptide elongation and solution-phase macrolactamization, followed by the removal of the protecting groups. Synthetic and demonstrated inhibitory effects on the growth of with minimum inhibitory

  本文报道了从放线菌UTG9属中分离得到的抗菌环六​​肽硝基磷酰胺A()和B()的全合成。合成涉及固相肽延伸和溶液相大环内酰胺化，然后除去保护基团。使用肉汤微量稀释法测定的合成和证明的生长抑制作用，最小抑制浓度 (MIC) 值分别为 8 μg/mL 和 16 μg/mL。
• Synthesis of Tripeptides Containing <scp>d</scp>-Trp Substituted at the Indole Ring, Assessment of Opioid Receptor Binding and in Vivo Central Antinociception
  作者：Rossella De Marco、Andrea Bedini、Santi Spampinato、Luca Gentilucci

  DOI：10.1021/jm5002925

  日期：2014.8.14

  The noncationizable tripeptide Ac-D-Trp-Phe-GlyNH2 was recently proposed as a novel minimal recognition motif for μ-opioid receptor. The introduction of different substituents (methyl, halogens, nitro, etc.) at the indole of D-Trp significantly influenced receptor affinities and resulted in serum stability and in a measurable effect on central antinociception in mice after ip administration.