2(S)-N-(tert-butoxycarbonyl)-2'-formyl tryptophan | 927189-97-7

• 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: 2(S)-N-(tert-butoxycarbonyl)-2'-formyl tryptophan
• 英文别名: 2-((tert-butoxycarbonyl)amino)-3-(2-formyl-1H-indol-3-yl)propanoic acid；Boc-2-formyl-L-Trp-OH；N-Boc-2-formyl-Trp-OH；(2S)-3-(2-formyl-1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 927189-97-7
• 化学式: C₁₇H₂₀N₂O₅
• 分子量: 332.356
• InChiKey: AXBUJPDIJCPVAT-ZDUSSCGKSA-N

物化性质

• 沸点：
  586.6±50.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2(S)-N-(tert-butoxycarbonyl)-2'-formyl tryptophan 在 吡啶 、 sodium cyanoborohydride 、 magnesium sulfate 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2(S)-benzyl [4-[(tert-butoxycarbonyl)amino]-3-oxo-3,4,5,10-tetrahydroazepino[3,4-b]indol-2(1H)-yl]-acetate
  参考文献：
  名称：

  4-氨基-3-氧代-四氢氮杂环庚烷[3,4- b ]吲哚的合成：新的构象受约束的Trp类似物

  摘要：

  据报道，色氨酸类似物的合成已通过七元内酰胺的形成限制了其构象。Boc-四氢-β-咔啉-3-羧酸的SeO 2氧化制得Boc保护的2'-甲酰基色氨酸。使用氰基硼氢化钠用多种胺和氨基酸酯进行还原胺化，然后将其闭环成目标化合物。约束的Trp衍生物已被掺入内啡肽1阿片肽序列中，以探测其生物活性构象。

  DOI：

  10.1016/j.tet.2006.11.069
• 作为产物：
  描述：

  (S)-2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚-3-羧酸 在 selenium(IV) oxide 、 三乙胺 作用下， 生成 2(S)-N-(tert-butoxycarbonyl)-2'-formyl tryptophan
  参考文献：
  名称：

  通过Ugi反应高度非对映选择性合成1-氨基甲酰基-4-氨基吲哚并a庚酮衍生物

  摘要：

  描述了一种用于高非对映选择性合成1-氨基甲酰基-4-氨基-1,2,4,5-四氢吲哚并[2,3 - c ]氮杂-3-酮衍生物的一锅法程序。使用2-甲酰基-L-色氨酸作为双功能结构单元，开发了无催化剂的Ugi-三组分反应（Ugi-3CR），以高收率和优异的非对映异构体过量提供了三取代的吲哚并ze庚酮。

  DOI：

  10.1021/ol402940x

文献信息

• Design of Novel Neurokinin 1 Receptor Antagonists Based on Conformationally Constrained Aromatic Amino Acids and Discovery of a Potent Chimeric Opioid Agonist-Neurokinin 1 Receptor Antagonist
  作者：Steven Ballet、Debby Feytens、Koen Buysse、Nga N. Chung、Carole Lemieux、Suneeta Tumati、Attila Keresztes、Joost Van Duppen、Josephine Lai、Eva Varga、Frank Porreca、Peter W. Schiller、Jozef Vanden Broeck、Dirk Tourwé

  DOI：10.1021/jm1016285

  日期：2011.4.14

  A screening of conformationally constrained aromatic amino acids as base cores for the preparation of new NK1 receptor antagonists resulted in the discovery of three new NK1 receptor antagonists, 19 [Ac-Aba-Gly-NH-3′,5′-(CF3)2-Bn], 20 [Ac-Aba-Gly-NMe-3′,5′-(CF3)2-Bn], and 23 [Ac-Tic-NMe-3′,5′-(CF3)2-Bn], which were able to counteract the agonist effect of substance P, the endogenous ligand of NK1R

  筛选构象受限的芳香族氨基酸作为制备新 NK1 受体拮抗剂的基础核心，发现了三种新的 NK1 受体拮抗剂，19 [Ac-Aba-Gly-NH-3',5'-(CF 3 ) 2 -Bn]、20 [Ac-Aba-Gly-NMe-3',5'-(CF 3 ) 2 -Bn] 和23 [Ac-Tic-NMe-3',5'-(CF 3 ) 2 -Bn]，能够抵消物质 P（NK1R 的内源性配体）的激动作用。该系列中最活跃的 NK1 拮抗剂，20 [Ac-Aba-Gly-NMe-3',5'-(CF 3 ) 2-Bn]，然后用于设计一种新型、有效的嵌合阿片类激动剂-NK1受体拮抗剂，35 [Dmt - d -Arg-Aba-Gly-NMe-3',5'-(CF 3 ) 2 -Bn ]，它结合了已建立的 Dmt 1 -DALDA 激动剂阿片类药效团（H- Dmt - d -Arg-Phe-Lys-NH 2）和20的 N
• T3P-Promoted, Mild, One-Pot Syntheses of Constrained Polycyclic Lactam Dipeptide Analogues via Stereoselective Pictet–Spengler and Meyers Lactamization Reactions
  作者：Mouhamad Jida、Olivier Van der Poorten、Karel Guillemyn、Zofia Urbanczyk-Lipkowska、Dirk Tourwé、Steven Ballet

  DOI：10.1021/acs.orglett.5b02145

  日期：2015.9.18

  diastereoselective synthesis of constrained 7,5- and 7,6-fused azabicycloalkanes. Using 2-formyl-L-tryptophan and 2-formyl-l-phenylalanine as bielectrophilic building blocks, T3P-mediated Pictet–Spengler and Meyers lactamization reactions were developed to present chiral and polycyclic aminoindolo- and aminobenzazepinone compounds in excellent yields. The conformationally constrained compounds can serve as

  描述了一种新的方便，温和的一锅法，用于受约束的7,5-和7,6-稠合的氮杂双环烷烃的非对映选择性合成。使用2-甲酰基-L-色氨酸和2-甲酰基-l-苯丙氨酸作为双亲电子构件，开发了T3P介导的Pictet-Spengler和Meyers内酰胺化反应，以优异的产率提供了手性和多环氨基吲哚-和氨基苯并ze庚酮化合物。构象受限的化合物可以用作拟肽研究或多杂环特权支架的模板。
• Oxidation of Tetrahydro-β-carbolines by Persulfate
  作者：Haijun Chen、Fu Ye、Jing Luo、Yu Gao

  DOI：10.1021/acs.orglett.9b02772

  日期：2019.9.20

  The development of persulfate-mediated oxidation of tetrahydro-β-carbolines is reported. This mild reaction facilitates the formation of a variety of 2-formyl N-substituted tryptamines and the related derivatives as key intermediates in moderate to excellent yields. The method is applicable to direct last-stage oxidation of two interesting pharmaceuticals, Cialis and evodiamine.

  据报道过硫酸盐介导的四氢-β-咔啉氧化反应的发展。这种温和的反应有助于以中等至优异的产率形成各种2-甲酰基N-取代的色胺和相关衍生物作为关键中间体。该方法适用于两种有趣的药物Cialis和evodiamine的直接最后阶段氧化。
• Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens
  作者：Gaëlle Simon、Christopher Bérubé、Normand Voyer、Daniel Grenier

  DOI：10.1016/j.bmc.2018.11.042

  日期：2019.6

  Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure-activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.
• Azepinone-Containing Tetrapeptide Analogues of Melanotropin Lead to Selective <i>h</i>MC4R Agonists and <i>h</i>MC5R Antagonist
  作者：Olivier Van der Poorten、Krisztina Fehér、Koen Buysse、Debby Feytens、Ioanna Zoi、Steven D. Schwartz、José C. Martins、Dirk Tourwé、Minying Cai、Victor J. Hruby、Steven Ballet

  DOI：10.1021/ml500436s

  日期：2015.2.12

  To address the need for highly potent, metabolically stable, and selective agonists, antagonists, and inverse agonists at the melanocortin receptor subtypes, conformationally constrained indolo- and benzazepinone residues were inserted into the α-MSH pharmacophore, His(6)-Phe(7)-Arg(8)-Trp(9)-domain. Replacement of His(6) by an aminoindoloazepinone (Aia) or aminobenzazepinone (Aba) moiety led to hMC4R and hMC5R selective agonist and antagonist ligands, respectively (tetrapeptides 1 to 3 and 4, respectively). In peptides 1 to 3 and depending on the para-substituent of the d-Phe residue in position 2, the activity goes from allosteric partial agonism (1, R = H) to allosteric full agonism (2, R = F) and finally allosteric partial agonism (3, R = Br).