氨甲酸,[1-甲酰基-2-(1H-吲哚-3-基)乙基]-,苯基甲基酯,(R)- | 139091-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 氨甲酸,[1-甲酰基-2-(1H-吲哚-3-基)乙基]-,苯基甲基酯,(R)-
• 英文名称: (S)-benzyl (1-(indol-3-yl)-3-oxopropan-2-yl)carbamate
• 英文别名: (S)-Benzyl 1-(indol-3-yl)-3-oxopropan-2-ylcarbamate；Z-L-tryptophanal；Cbz-L-tryptophal；[(S)-1-Formyl-2-(1H-indol-3-yl)-ethyl]-carbamic acid benzyl ester；benzyl N-[(2S)-1-(1H-indol-3-yl)-3-oxopropan-2-yl]carbamate
• CAS: 139091-30-8；109364-32-1
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: LYPLMBSZQGCKEL-INIZCTEOSA-N

物化性质

• 沸点：
  556.5±50.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氨甲酸,[1-甲酰基-2-(1H-吲哚-3-基)乙基]-,苯基甲基酯,(R)- 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -20.0~20.0 ℃ 、275.79 kPa 条件下， 反应 124.0h， 生成 (4aS,5R)-2-benzyl-5-[(4S,5R)-5-cyano-4-(indol-3-yl)methyl-2-oxoimidazolidin-1-yl]-1,3-dioxoperhydropyrido[1,2-c]pyrimidine
  参考文献：
  名称：

  5-(Tryptophyl)amino-1,3-dioxoperhydropyrido[1,2-c]pyrimidine-Based Potent and Selective CCK₁ Receptor Antagonists:  Structural Modifications at the Tryptophan Domain

  摘要：

  Analogues of the previously reported potent and highly selective CCK1 receptor antagonist (4aS,5R)-2-benzyl-5-(N-Boc-tryptophyl)amino-1,3-dioxoperhyropyrido-[1,2-c]pyrimidine (2a) were prepared to explore the structural requirements at the Boc-tryptophan domain for CCK1 receptor affinity. Structural modifications of 2a involved the Trp side chain, its conformational freedom, the Boc group, and the carboxamide bond. Results of the CCK binding and in vitro functional activity evaluation showed three highly strict structural requirements: the type and orientation of the Trp side chain, the H-bonding acceptor carbonyl group of the carboxamide bond, and the presence of the Trp amino protection Boc. Replacement of this acid-labile group with 3,3-dimethylbutyryl or tert-butylaminocarbonyl conferred acid stability to analogues 14a and 15a, which retained a high potency and selectivity in binding to CCK1 receptors, as well as an in vivo antagonist activity against the acute pancreatitis induced by caerulein in rats. Oral administration of compounds 14a and 15a also produced a lasting antagonism to the hypomotility induced by CCK-8 in mice, suggesting a good bioavailability and metabolic stability.

  DOI：

  10.1021/jm991078x
• 作为产物：
  描述：

  (S)-N-benzyloxycarbonyl-L-tryptophan methyl ester 在 二异丁基氢化铝 作用下， 以73%的产率得到氨甲酸,[1-甲酰基-2-(1H-吲哚-3-基)乙基]-,苯基甲基酯,(R)-
  参考文献：
  名称：

  细胞松弛素合成：细胞松弛素G的全合成

  摘要：

  细胞松弛素G（2），一种具有分子色Diels-Alder反应形成11元环的[11]细胞松弛素，在C（3）处具有色氨酸衍生的吲哚甲基取代基。

  DOI：

  10.1039/c39860001447

文献信息

• Cytochalasan synthesis: total synthesis of cytochalasin G
  作者：Hazel Dyke、Robert Sauter、Patrick Steel、Eric J. Thomas

  DOI：10.1039/c39860001447

  日期：——

  Cytochalasin G(2), an [11]cytochalasan with a tryptophan derived indolymethyl substituent at C(3) has been synthesized using an intramolecular Diels–Alder reaction to form the 11-membered ring.

  细胞松弛素G（2），一种具有分子色Diels-Alder反应形成11元环的[11]细胞松弛素，在C（3）处具有色氨酸衍生的吲哚甲基取代基。
• Efficient Access to Enantiopure γ⁴-Amino Acids with Proteinogenic Side-Chains and Structural Investigation of γ⁴-Asn and γ⁴-Ser in Hybrid Peptide Helices
  作者：Sandip V. Jadhav、Rajkumar Misra、Sumeet K. Singh、Hosahudya N. Gopi

  DOI：10.1002/chem.201302732

  日期：2013.11.25

  to fold into ordered helical structures. As amino acid side‐chain functional groups play a crucial role in the biological context, the objective of this study was to investigate efficient synthesis of γ4‐residues with functional proteinogenic side‐chains and their structural analysis in hybrid‐peptide sequences. Here, the efficient and enantiopure synthesis of various N‐ and C‐terminal free‐γ4‐residues

  由α-和β-氨基酸组成的杂合肽最近已成为一类新型的肽折叠剂。相比较而言，γ的组成γ-和混合γ-肽4 -氨基酸比其β-对应物少的研究。然而，最近的研究表明，γ 4 -氨基酸有较高的倾向折叠成有序的螺旋结构。作为氨基酸侧链的官能团起到生物上下文中的关键作用，本研究的目的是调查γ的有效合成4 -残基与官能蛋白原侧链和在混合的肽序列的结构分析。在这里，各种N-末端和C-末端游离-γ的有效和对映体纯合成4-残基，从苄基酯（COOBzl）起始Ñ -Cbz保护的（ë）- α，报道β不饱和γ氨基通过在单锅催化氢化多个氢解和双键还原酸。8未受保护的γ的结晶构象，4 -氨基酸（γ 4 -Val，γ 4 -Leu，γ 4 -Ile，γ 4 -Thr（O吨丁基），γ 4 -Tyr，γ 4 -Asp（O吨卜），γ 4 -Glu（O吨丁基），和γ-AIB）显示，这些氨基酸通过一个螺旋利于笨拙沿着中心Ç构象γ  Ç β键。来研究γ行为4
• Pyrazine alkaloids via dimerization of amino acid-derived α-amino aldehydes: biomimetic synthesis of 2,5-diisopropylpyrazine, 2,5-bis(3-indolylmethyl)pyrazine and actinopolymorphol C
  作者：Sandhya Badrinarayanan、Jonathan Sperry

  DOI：10.1039/c2ob06935k

  日期：——

  of amino acid-derived alpha-amino aldehydes provides a short, biomimetic synthesis of several 2,5-disubstituted pyrazine natural products. The alpha-amino aldehyde intermediates were generated in situ by the hydrogenolysis of their Cbz-derivatives. It was found that a judicious choice of reaction solvent facilitated hydrogenolysis, dimerization and oxidation to the natural product in a one-pot operation

  氨基酸衍生的α-氨基醛的二聚化提供了几种2，5-二取代的吡嗪天然产物的短时仿生合成。α-氨基醛中间体是通过对其Cbz衍生物进行氢解而原位生成的。已经发现，明智地选择反应溶剂可以在一锅操作中促进氢解，二聚和氧化为天然产物。该方法论证明了自然界中最近提出的替代性生物合成路线对2,5-二取代吡嗪的可行性。此外，这项工作描述了一种新颖，简洁的方法，该方法可从易得的廉价氨基酸衍生而来的α-氨基醛制取吡嗪。
• Synthesis and biological activities of pseudopeptide analogs of the C-terminal heptapeptide of cholecystokinin. On the importance of the peptide bonds
  作者：Marc Rodriguez、Marie Francoise Lignon、Marie Christine Galas、Pierre Fulcrand、Christiane Mendre、Andre Aumelas、Jeanine Laur、Jean Martinez

  DOI：10.1021/jm00391a017

  日期：1987.8

  A series of pseudopeptide analogues of the C-terminal heptapeptide of cholecystokinin in which each peptide bond, one at a time, has been replaced by a CH2NH bond were synthesized: Z-Tyr(SO3-)-Nle-Gly-Trp-Nle-Asp psi-(CH2NH)Phe-NH2 (1), Z-Tyr(SO3-)-Nle-Gly-Trp-Nle psi (CH2NH)Asp-Phe-NH2 (2), Z-Tyr(SO3-)-Nle-Gly-Trp psi-(CH2NH)Nle-Asp-Phe-NH2 (3), Z-Tyr(SO3-)-Nle-Gly psi(CH2NH)Trp-Nle-Asp-Phe-NH2 (4)

  合成了胆囊收缩素C端七肽的一系列伪肽类似物，其中每个肽键一次被一个CH2NH键取代：Z-Tyr（SO3-）-Nle-Gly-Trp-Nle- Asp psi-（CH2NH）Phe-NH2（1），Z-Tyr（SO3-）-Nle-Gly-Trp-Nle psi（CH2NH）Asp-Phe-NH2（2），Z-Tyr（SO3-）-Nle -Gly-Trp psi-（CH2NH）Nle-Asp-Phe-NH2（3），Z-Tyr（SO3-）-Nle-Gly psi（CH2NH）Trp-Nle-Asp-Phe-NH2（4），Z- Tyr（SO3-）-Nle psi-（CH2NH）Gly-Trp-Nle-Asp-Phe-NH2（5），Z-Tyr（SO3-）-Met-Gly-Trp-Nle-Asp psi（CH2NH）Phe- NH2（6），Z-Tyr-（SO3-）-Met-Gly-Trp-Nle psi（
• Tin triflate-mediated total synthesis of circumdatin F, sclerotigenin, asperlicin C, and other quinazolino[3,2-a][1,4]benzodiazepines
  作者：Ming-Chung Tseng、Chi-Yu Lai、Yu-Wan Chu、Yen-Ho Chu

  DOI：10.1039/b813880j

  日期：——

  cyclizations of bis(anthranilate)-containing tripeptide precursors to afford the total syntheses of 7-substituted quinazolino[3,2-a][1,4]benzodiazepinediones (1a-f), including natural products circumdatin F (1a), sclerotigenin (1b), and asperlicin C (1c), were achieved with good overall isolated yields (23-62%).

  使用三氟甲磺酸锡（作为有效的路易斯酸）和微波，直接对含双（邻氨基苯甲酸酯）的三肽前体进行双环化，以提供7-取代的喹唑啉基[3,2-a] [1,4]苯并二氮杂二酮（1a -f），包括环丁抑素F（1a），硬化素（1b）和曲霉菌素C（1c）的天然产物，均具有良好的总体分离收率（23-62％）。