1-bromo-3-(aminomethyl)adamantane hydrochloride

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1-bromo-3-(aminomethyl)adamantane hydrochloride
• 英文别名: (3-Bromoadamantan-1-yl)methanamine hydrochloride；(3-bromo-1-adamantyl)methanamine;hydrochloride
• 化学式: C₁₁H₁₈BrN*ClH
• mdl: MFCD22565925
• 分子量: 280.636
• InChiKey: QYRIAQNECLTYOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-3-(aminomethyl)adamantane hydrochloride 在 N-甲基吗啉 、 硫酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.03h， 生成 (S)-2-{(S)-2-[(3-{[(S)-2-tert-Butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-methyl}-adamantane-1-carbonyl)-amino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid
  参考文献：
  名称：

  Tumor-Cell-Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids:  Design, Synthesis, and in Vitro Antitumor Activity

  摘要：

  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.

  DOI：

  10.1021/jm051026+

文献信息

• 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.