1,1-dimethylethyl (R)-2,2-dimethyl-4-phenoxymethyl-3-oxazolidinecarboxylate | 929555-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1-dimethylethyl (R)-2,2-dimethyl-4-phenoxymethyl-3-oxazolidinecarboxylate
• 英文别名: (R)-2,2-dimethyl-4-phenoxymethyloxazolidine-3-carboxylic acid tert-butyl ester；(R)-2,2-dimethyl-4-phenoxymethyl-oxazolidine-3-carboxylic acid tert-butyl ester；tert-butyl (4R)-2,2-dimethyl-4-(phenoxymethyl)-1,3-oxazolidine-3-carboxylate
• CAS: 929555-72-6
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: LVEICBMEUCOIQC-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl (R)-2,2-dimethyl-4-phenoxymethyl-3-oxazolidinecarboxylate 在 盐酸 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 以66%的产率得到(S)-2-amino-3-phenoxypropan-1-ol
  参考文献：
  名称：

  WO2008/92785

  摘要：

  公开号：
• 作为产物：
  描述：

  Boc-L-丝氨酸甲酯 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 4.08h， 生成 1,1-dimethylethyl (R)-2,2-dimethyl-4-phenoxymethyl-3-oxazolidinecarboxylate
  参考文献：
  名称：

  Synthesis of Novel 2,3,4-trisubstituted-oxazolidine Derivatives and In Vitro Cytotoxic Evaluation

  摘要：

  我们之前报道了发现于白血病细胞的细胞毒性和促凋亡的命中化合物1,1-二甲基乙基(S)-2,2-二甲基-4-[(3-硝基苯氧基)甲基]-3-恶唑烷羧酸酯1。在本次工作中，我们描述了该命中化合物的25种衍生物的合成，通过改变恶唑烷环上的取代基或立体化学，并在人类癌细胞系中评估了它们的活性。其中六种化合物对HL60早幼粒细胞白血病细胞显示出显著活性，IC50在低微摩尔范围内（4-18 μM），三种化合物对MDA-MB231乳腺癌细胞显示出活性（25-37 μM）。同时，也对正常细胞PBMC（人外周血单个核细胞）进行了体外细胞毒性评估。化合物7e（p-NO2, S）和7m（p-COOCH3, S）对HL60（4和5 μM）和MDA-MB231（37和25 μM）显示出良好的抗增殖活性，而不影响PBMC中淋巴细胞的增殖，表明对正常细胞的毒性较低。此外，化合物7e在50 μM下诱导约100%的HL60细胞发生DNA断裂。在这种情况下，其效力超过了7m和先导物1，这表明化合物7e具有很高的促凋亡潜力。

  DOI：

  10.2174/15734064113096660057

文献信息

• 2-Aminooxazolines as TAAR1 ligands
  申请人：Galley Guido

  公开号：US20080261920A1

  公开（公告）日：2008-10-23

  The invention relates to compounds of formula I wherein X, Y, R 1 , R 2 , and n are as defined herein or to a pharmaceutically suitable acid addition salt thereof. The invention also relates to pharmaceutical compositions containing such compounds and methods for the treatment of diseases related to the biological function of the trace amine associated receptors, which diseases include depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders, schizophrenia, neurological diseases, Parkinson's disease, neurodegenerative disorders, Alzheimer's disease, epilepsy, migraine, substance abuse and metabolic disorders, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及化合物I的公式，其中X，Y，R1，R2和n如本文所定义，或其药学上适宜的酸加盐。本发明还涉及含有这种化合物的制药组合物和治疗与微量胺相关受体的生物学功能相关的疾病的方法，这些疾病包括抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍、压力相关障碍、精神障碍、精神分裂症、神经系统疾病、帕金森病、神经退行性疾病、阿尔茨海默病、癫痫、偏头痛、物质滥用和代谢性疾病、进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍以及心血管疾病。
• 2-AMINOOXAZOLINES AS TAAR1 LIGANDS
  申请人：Galley Guido

  公开号：US20100120864A1

  公开（公告）日：2010-05-13

  The invention relates to compounds of formula I wherein X, Y, R 1 , R 2 , and n are as defined herein or to a pharmaceutically suitable acid addition salt thereof. The invention also relates to pharmaceutical compositions containing such compounds and methods for the treatment of diseases related to the biological function of the trace amine associated receptors, which diseases include depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders, schizophrenia, neurological diseases, Parkinson's disease, neurodegenerative disorders, Alzheimer's disease, epilepsy, migraine, substance abuse and metabolic disorders, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及式I的化合物，其中X，Y，R1，R2和n如本文所定义，或其药学适宜的酸加盐。本发明还涉及含有此类化合物的制药组合物，以及用于治疗与微量胺相关受体的生物学功能相关的疾病的方法，这些疾病包括抑郁症，焦虑症，双相情感障碍，注意力缺陷多动障碍，应激相关障碍，精神疾病，精神分裂症，神经疾病，帕金森病，神经退行性疾病，阿尔茨海默病，癫痫，偏头痛，物质滥用和代谢性疾病，进食障碍，糖尿病，糖尿病并发症，肥胖症，血脂异常，能量消耗和吸收障碍，体温稳态障碍和功能障碍，睡眠和生物钟节律障碍以及心血管疾病。
• 2-aminooxazolines as TAAR1 ligands
  申请人：Galley Guido

  公开号：US08604061B2

  公开（公告）日：2013-12-10

  The invention relates to compounds of formula I wherein X, Y, R1, R2, and n are as defined herein or to a pharmaceutically suitable acid addition salt thereof. The invention also relates to pharmaceutical compositions containing such compounds and methods for the treatment of diseases related to the biological function of the trace amine associated receptors, which diseases include depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders, schizophrenia, neurological diseases, Parkinson's disease, neurodegenerative disorders, Alzheimer's disease, epilepsy, migraine, substance abuse and metabolic disorders, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及式I的化合物，其中X、Y、R1、R2和n如本文所定义，或其药学上适宜的酸加盐。本发明还涉及含有这种化合物的制药组合物和治疗与微量胺相关受体的生物学功能相关的疾病的方法，这些疾病包括抑郁症、焦虑症、躁郁症、注意力缺陷多动障碍、与压力相关的疾病、精神疾病、精神分裂症、神经系统疾病、帕金森病、神经退行性疾病、阿尔茨海默病、癫痫、偏头痛、物质滥用和代谢性疾病、进食障碍、糖尿病、糖尿病并发症、肥胖症、脂质代谢异常、能量消耗和吸收障碍、体温稳态障碍和功能障碍、睡眠和昼夜节律障碍以及心血管疾病。
• Complete Structure Elucidation of Shishididemniols, Complex Lipids with Tyramine-Derived Tether and Two Serinol Units, from a Marine Tunicate of the Family Didemnidae
  作者：Hirotsugu Kobayashi、Jun'ichiro Ohashi、Tsuyoshi Fujita、Takashi Iwashita、Yoichi Nakao、Shigeki Matsunaga、Nobuhiro Fusetani

  DOI：10.1021/jo062013m

  日期：2007.2.1

  Two new serinolipid derivatives, shishididemniols A (1) and B (2), were isolated as antibacterial constituents of a tunicate of the family Didemnidae. The structure of 1 was elucidated by interpretation of spectral data and the application of the modified Mosher method to 1 and its suitable degradation products. Compound 2 was the chlorohydrin of 1. Compounds 1 and 2 exhibited antibacterial activity against fish pathogenic bacterium Vibrio anguillarum.
• NOVEL 2-AMINOOXAZOLINES AS TAAR1 LIGANDS FOR CNS DISORDERS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2114906A1

  公开（公告）日：2009-11-11