(αR)-α-氨基三环[3.3.1.13,7]癸烷-1-乙酸 | 59768-71-7

• 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: (αR)-α-氨基三环[3.3.1.13,7]癸烷-1-乙酸
• 英文名称: R-amino-(1-adamantanyl)acetic acid
• 英文别名: (R)-2-(1-adamantyl)glycine；(R)-(1-adamantyl)glycine；D-(adamant-1-yl)glycine；(2R)-2-(1-adamantyl)-2-azaniumylacetate
• CAS: 59768-71-7；60256-21-5；95853-35-3；100926-41-8
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: NJRFVURYVWPLKB-SPPFVYQKSA-N

物化性质

• 沸点：
  355.6±25.0 °C(Predicted)
• 密度：
  1.244

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (αR)-α-氨基三环[3.3.1.13,7]癸烷-1-乙酸 在 氯化亚砜 、 1-丙基磷酸酐 、 N,N-二异丙基乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 生成 ethyl (2S)-2-(1-adamantyl)-2-[[1-[[4-(trifluoromethyl)phenyl]methoxy]naphthalene-2-carbonyl]amino]acetate
  参考文献：
  名称：

  [EN] CFTR-MODULATING ARYLAMIDES
  [FR] ARYLAMIDES MODULANT CFTR

  摘要：

  本公开涉及杂环化合物，其药用可接受盐以及其制药制剂。还描述了此类化合物的组成以及在治疗由CFTR活性缺陷介导的疾病和症状的方法中的使用，特别是囊性纤维化。

  公开号：

  WO2021113808A1
• 作为产物：
  描述：

  (S)-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 在 palladium on activated charcoal ruthenium trichloride 、 sodium periodate 、 氢气 作用下， 以 甲醇 、 四氯化碳 、 水 、 乙腈 为溶剂， 20.0 ℃ 、202.65 kPa 条件下， 生成 (αR)-α-氨基三环[3.3.1.13,7]癸烷-1-乙酸
  参考文献：
  名称：

  Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: a combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution

  摘要：

  Alkylation of the cobalt(II) complex of ethyl acetoacetate with 1-bromoadamantane affords ethyl 2-(1-adamantyl)acetoacetate, which was converted into rac-(1-adamantyl)glycine 1 and rac-2-(1-adamantyl)-2-aminoethanol 7. This was separated into enantiomers by means of vinyl acetate in the presence of Pseudomonas cepacea. Configuration R was assigned to the enantiomerically pure aminoalcohol (R)-7 on the basis of X-ray diffraction data. Further oxidation of N-protected aminoalcohol (R)-8 afforded enantiomerically pure amino acid (R)-1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00428-6

文献信息

• Synthesis and Immunostimulating Properties of Novel Adamant-1-yl Tripeptides
  作者：Rosana Ribić、Lidija Habjanec、Branka Vranešić、Ruža Frkanec、Srđanka Tomić

  DOI：10.1002/cbdv.201100232

  日期：2012.4

  The aim of this work was to prepare L- and D-(adamant-1-yl)-Gly-L-Ala-D-isoGln peptides in order to study their adjuvant (immunostimulating) activities. Adjuvant activity of adamant-1-yl tripeptides was tested in the mouse model using ovalbumin as an antigen and in comparison to the peptidoglycan monomer (PGM; β-D-GlcNAc-(1→4)-D-MurNAc-L-Ala-D-isoGln-mesoDAP(εNH(2) )-D-Ala-D-Ala) and structurally related

  这项工作的目的是为了制备L-和D-（金刚烷基-1-基）-Gly-L-Ala-D-isoGln肽，以研究其佐剂（免疫刺激）活性。使用卵清蛋白作为抗原在小鼠模型中测试了金刚烷-1-基三肽的佐剂活性，并与肽聚糖单体（PGM;β-D-GlcNAc-（1→4）-D-MurNAc-L-Ala- D-isoGln-mesoDAP（εNH（2））-D-Ala-D-Ala）和结构相关的金刚烷基-2-基三肽。
• Tumor-Cell-Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids:  Design, Synthesis, and in Vitro Antitumor Activity
  作者：Štefica Horvat、Kata Mlinarić-Majerski、Ljubica Glavaš-Obrovac、Andreja Jakas、Jelena Veljković、Saška Marczi、Goran Kragol、Maja Roščić、Marija Matković、Andrea Milostić-Srb

  DOI：10.1021/jm051026+

  日期：2006.6.1

  A series of new peptides (8-25) containing different unnatural amino acids of the adamantane type (1-6), was synthesized. Possible cytotoxic activity on human cervical adenocarcinoma ( HeLa), larynx carcinoma (HEp-2), colon carcinomas (HT-29, Caco-2), poorly differentiated cells from lymph node metastasis of colon carcinoma (SW-620), mammary gland adenocarcinoma (MCF-7), and melanoma (HBL) cells were tested by the MTT assay. The results were compared with the effect of methionine-enkephalin (Tyr-GlyGly-Phe-Met, or opioid growth factor, OGF), and its shorter N-terminal fragments. Peptide analogues containing CRR-dialkylated glycine (Aaa1, 1) or CR-alkylated glycine (Aaa2, 2) amino acid residues showed antitumor activity against melanoma, larynx carcinoma, colon carcinomas, and colon metastasis cell lines in vitro. The pentapeptide Tyr-(R,S)-Aaa2-Gly-Phe-Met (18) was the most effective analogue especially against the most antitumor drug-resistant cell lines HEp-2 and SW-620. Apoptosis as a mode of cell death was confirmed in these tumor cells after exposure to pentapeptide 18.
• Krasutskii, P. A.; Semenova, I. G.; Novikova, M. I., Journal of Organic Chemistry USSR (English Translation), 1985, p. 1327 - 1332
  作者：Krasutskii, P. A.、Semenova, I. G.、Novikova, M. I.、Yurchenko, A. G.、Tikhonov, V. P.、et al.

  DOI：——

  日期：——