N-acetyl-7'-bromo-DL-tryptophan | 75816-18-1

• 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-acetyl-7'-bromo-DL-tryptophan
• 英文别名: acetyl-7-bromo-DL-tryptophan；N-Ac-(7'-Br-Trp)-OH；Ac-7'-Br-Trp-OH；N-acetyl-7-bromo-dl-tryptophan；2-acetamido-3-(7-bromo-1H-indol-3-yl)propanoic acid
• CAS: 75816-18-1
• 化学式: C₁₃H₁₃BrN₂O₃
• 分子量: 325.162
• InChiKey: TZHTUVZZNLKONV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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-acetyl-7'-bromo-DL-tryptophan 在 重氮甲烷 、 recombinant Escherichia coli D-aminoacylase 、 cobalt chloride hexahydrate 、 lithium hydroxide 作用下， 以 乙醚 、 苯 为溶剂， 反应 48.0h， 生成 Nb-methoxycarbonyl-7-bromo-D-tryptophan methyl ester
  参考文献：
  名称：

  (+)-灵芝胺的全合成指导结构解析

  摘要：

  解谜：全合成在立体化学的阐明和复杂的聚合天然产物精神四胺的构成验证中发挥了关键作用。该路线具有三个强大的组装过程，可进行四轮全合成引导结构确定。对这种生物碱的追求也导致了吲哚-苯胺偶联的改进程序和精神三胺的高效对映选择性合成。

  DOI：

  10.1002/anie.201008048
• 作为产物：
  描述：

  7-溴二氢吲哚 在 salcomine 、 氧气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N-acetyl-7'-bromo-DL-tryptophan
  参考文献：
  名称：

  通过N-甲酰吲哚啉的合成制备7-卤代吲哚，并尝试将其用于合成氯肽的右侧片段。

  摘要：

  以N-甲酰吲哚啉为关键反应，合成了7位取代的（Cl，Br，I）吲哚。通过使用由通过上述方法获得的每个7-取代的吲哚（I，Br）衍生的（R）-7'-碘和7'-溴色氨酸，合成了用于氯肽的右侧部分的两个前体三肽。

  DOI：

  10.1248/cpb.54.788

文献信息

• Total synthesis of ent-(−)-azonazine using a biomimetic direct oxidative cyclization and structural reassignment of natural product
  作者：Ji-Chen Zhao、Shun-Ming Yu、Hai-Bo Qiu、Zhu-Jun Yao

  DOI：10.1016/j.tet.2014.03.061

  日期：2014.5

  the first total synthesis of ent-(−)-azonazine. Based on the physical evidences of synthesized diastereomer and enantiomer of azonazine, both the relative and absolute configurations of the natural product were revised. Two fluorinated azonazine derivatives were also synthesized in short convenient steps utilizing the same intermediate in this work. The established total synthesis opens a potential opportunity

  已经对仿生方法进行了研究和开发，以完全合成阿扎津嗪，阿扎津嗪是一种不寻常的海洋天然环肽，包含刚性的跨环10元环。成功开发了高价碘介导的直接氧化环化反应，并将其用于构建高度应变的核，这是耳鼻喉科首次全合成的关键步骤-（-）-氮杂嗪。根据合成的偶氮嗪非对映异构体和对映异构体的物理证据，对天然产物的相对和绝对构型进行了修订。在这项工作中，利用相同的中间体，还可以在短短的便捷步骤中合成出两种氟化的偶氮嗪衍生物。既定的全合成为研究天然阿氮嗪的结构-活性关系提供了潜在的机会。
• Synthesis of 5- and 7-bromotryptophan and of [5-bromotryptophan⁹]-β-corticotrophin-(1–24)-tetracosapeptide, a highly potent corticotrophin analogue
  作者：Mark C. Allen、Derek E. Brundish、Roy Wade

  DOI：10.1039/p19800001928

  日期：——

  The synthesis of 5- and 7-bromo-L-tryptophans via Fischer cyclisation of the appropriate bromophenylhydrazone of 4-acetamido-4,4-bis(ethoxycarbonyl)butanal is described. The title tetracosapeptide was synthesised using standard methods of stepwise and fragment condensation. The product was pure as judged by amino-acid analysis after acidic or enzymic hydrolysis and by high pressure liquid chromatography

  描述了通过4-乙酰氨基-4,4-双（乙氧基羰基）丁醛的适当溴苯phenyl的费歇尔环化的5-溴-L-色氨酸和7-溴-L-色氨酸的合成。使用逐步和片段缩合的标准方法合成标题四糖肽。通过酸性或酶水解后的氨基酸分析和高压液相色谱法判断产物是纯的。在分离的肾上腺细胞生物测定中，该肽的类固醇生成能力是Synacthen的2.4倍。
• Diazonamide a analog
  申请人：Harran G. Patrick

  公开号：US20070149583A1

  公开（公告）日：2007-06-28

  A specific diazonamide A analog and its salts and conjugates are effective in treating proliferative diseases.

  一种特定的二氮杂环胺A类似物及其盐和结合物在治疗增生性疾病方面具有效果。
• 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.
• Synthesis and biological evaluation of novel tryptoline derivatives as indoleamine 2,3-dioxygenase (IDO) inhibitors
  作者：Minoru Tanaka、Xin Li、Hidemasa Hikawa、Takafumi Suzuki、Katsuhiko Tsutsumi、Masashi Sato、Osamu Takikawa、Hideharu Suzuki、Yuusaku Yokoyama

  DOI：10.1016/j.bmc.2012.12.028

  日期：2013.3

  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.