(1S)-1-(6-chloropyridin-3-yl)ethanol | 1016228-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1S)-1-(6-chloropyridin-3-yl)ethanol
• 英文别名: (S)-1-(6-Chloropyridin-3-YL)ethan-1-OL
• CAS: 1016228-05-9
• 化学式: C₇H₈ClNO
• 分子量: 157.6
• InChiKey: PMPXQVZBQKUJRU-YFKPBYRVSA-N

物化性质

• 沸点：
  284.5±25.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S)-1-(6-chloropyridin-3-yl)ethanol 在 N-氯代丁二酰亚胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以72%的产率得到2-chloro-5-[(1R)-1-chloroethyl]pyridine
  参考文献：
  名称：

  WO2008/39139

  摘要：

  公开号：
• 作为产物：
  描述：

  2-氯-5-乙酰基吡啶 在 环己烷 、 二乙醇胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以88%的产率得到(1S)-1-(6-chloropyridin-3-yl)ethanol
  参考文献：
  名称：

  Substituted 7-Amino-5-thio-thiazolo[4,5-d]pyrimidines as Potent and Selective Antagonists of the Fractalkine Receptor (CX₃CR1)

  摘要：

  We have developed two parallel series, A and B, of CX(3)CR1 antagonists for the treatment of multiple sclerosis. By modifying the substituents on the 7-amino-5-thio-thiazolo[4,5-d]-pyrimidine core structure, we were able to achieve compounds with high selectivity for CX(3)CR1 over the closely related CXCR2 receptor. The structure-activity relationships showed that a leucinol moiety attached to the core-structure in the 7-position together with alpha-methyl branched benzyl derivatives in the 5-position displayed promising affinity, and selectivity as well as physicochemical properties, as exemplified by compounds 18a and 24h. We show the preparation of the first potent and selective orally available CX(3)CR1 antagonists.

  DOI：

  10.1021/jm3012273

文献信息

• The first total synthesis of (−)-mitragynine, an analgesic indole alkaloid in mitragyna speciosa
  作者：Hiromitsu Takayama、Moriyoshi Maeda、Satoshi Ohbayashi、Mariko Kitajima、Shin-ichiro Sakai、Norio Aimi

  DOI：10.1016/0040-4039(95)02022-h

  日期：1995.12

  Starting from an optically pure alcohol, (R)-(3), which was prepared by enzymatic hydrolysis of the racemic acetate (2) or enantioselective reduction of the ketone derivative (4), the chiral total synthesis of mitragynine (1), a major corynanthe-type indole alkaloid having an analgesic effect in Mitragyna speciosa, was accomplished.

  由光学纯的醇（R）-（3）起始，其是通过消旋乙酸外消旋体（2）或对映体选择性还原酮衍生物（4）进行手性全合成的米格炔宁（1）制备的。主要柯楠因型吲哚生物碱具有镇痛作用帽柱木桐，被完成。
• Novel Compounds 480
  申请人：Johansson Rolf

  公开号：US20080318981A1

  公开（公告）日：2008-12-25

  There are disclosed novel 5,7-disubstituted [1,3]thiazolo[4,5-d]pyrimidin-2(3H)-one derivatives of formula (I) wherein R 1 , R 2 , R 3 , R 4 and n are as defined in the specification, and pharmaceutically acceptable salts thereof, together with processes for their preparation, pharmaceutical compositions comprising them and their use in therapy. The compounds of formula (I) are CX 3 CR 1 receptor antagonists and are thereby particularly useful in the treatment or prophylaxis of neurodegenerative disorders, demyelinating disease, cardio- and cerebrovascular atherosclerotic disorders, peripheral artery disease, rheumatoid arthritis, pulmonary diseases such as COPD, asthma or pain.

  本发明公开了一种新型的5,7-二取代[1,3]噻唑并[4,5-d]嘧啶-2(3H)-酮衍生物(I)，其中R1、R2、R3、R4和n在规范中定义，以及其药学上可接受的盐，以及它们的制备方法、含有它们的制药组合物和它们在治疗中的应用。化合物(I)是CX3CR1受体拮抗剂，因此在治疗或预防神经退行性疾病、脱髓鞘疾病、心血管和脑血管动脉粥样硬化性疾病、周围动脉疾病、类风湿性关节炎、COPD、哮喘或疼痛方面特别有用。
• 5,7-DISUBSTITUTED[1.3]THIAZOLO[4,5-d]PYRIMIDIN-2(3H)-AMINE DERIVATIVES AND THEIR USE IN THERAPY
  申请人：Johansson Rolf

  公开号：US20100035899A1

  公开（公告）日：2010-02-11

  There are disclosed novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives of formula (I) wherein R 1 , R 2 , R 3 , R 4 and n are as defined in the specification, and pharmaceutically acceptable salts thereof, together with processes for their preparation, pharmaceutical compositions comprising them and their use in therapy. The compounds of formula (I) are CX 3 CR1 receptor antagonists and are thereby particularly useful in the treatment or prophylaxis of neurodegenerative disorders, demyelinating disease, cardio- and cerebrovascular atherosclerotic disorders, peripheral artery disease, rheumatoid arthritis, pulmonary diseases such as COPD, asthma or pain.

  公开了一种新的式(I)的5-取代7-氨基-[1,3]噻唑[4,5-d]嘧啶衍生物，其中R1、R2、R3、R4和n如规范中所定义的，以及其药学上可接受的盐，以及它们的制备方法、包含它们的制药组合物和它们在治疗中的用途。式(I)化合物是CX3CR1受体拮抗剂，因此在神经退行性疾病、脱髓鞘性疾病、心血管和脑血管动脉粥样硬化性疾病、外周动脉疾病、类风湿性关节炎、COPD、哮喘或疼痛的治疗或预防中特别有用。
• 5,7-DISUBSTITUTED THIAZOLO[4,5-D]PYRIMIDINES FOR THE SELECTIVE INHIBITION OF CHEMOKINE RECEPTORS
  申请人：Johansson Rolf

  公开号：US20110105537A1

  公开（公告）日：2011-05-05

  There are disclosed novel 5,7-disubstituted [1,3]thiazolo[4,5-d]pyrimidin-2(3H)-one derivatives of formula (I) wherein R 1 , R 2 , R 3 , R 4 and n are as defined in the specification, and pharmaceutically acceptable salts thereof, together with processes for their preparation, pharmaceutical compositions comprising them and their use in therapy. The compounds of formula (I) are CX 3 CR1 receptor antagonists and are thereby particularly useful in the treatment or prophylaxis of neurodegenerative disorders, demyelinating disease, cardio- and cerebrovascular atherosclerotic disorders, peripheral artery disease, rheumatoid arthritis, pulmonary diseases such as COPD, asthma or pain.

  本发明揭示了一种新的5,7-二取代[1,3]噻唑并[4,5-d]嘧啶-2(3H)-酮衍生物(I)，其中R1、R2、R3、R4和n如规范所定义，以及其药学上可接受的盐，还揭示了它们的制备方法、包含它们的制药组合物以及它们在治疗中的使用。公式(I)化合物是CX3CR1受体拮抗剂，因此在神经退行性疾病、脱髓鞘性疾病、心血管和脑血管动脉粥样硬化性疾病、周围动脉疾病、类风湿性关节炎、COPD、哮喘或疼痛的治疗或预防中特别有用。
• WO2008/39139
  申请人：——

  公开号：——

  公开（公告）日：——