(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-butane-1,2-diol | 134362-04-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-butane-1,2-diol
• 英文别名: 3-(S)-amino-4-cyclohexyl-1-cyclopropyl-butane-1-(S),2-(R)-diol；(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol；(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropylbutane-1,2-diol
• CAS: 134362-04-2
• 化学式: C₁₃H₂₅NO₂
• 分子量: 227.347
• InChiKey: QCHGPWDFRLYQLQ-RWMBFGLXSA-N

物化性质

• 熔点：
  139.1-140.9 °C
• 沸点：
  405.2±25.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-butane-1,2-diol 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-(R)-amino-N-[(1-(S)-cyclohexylmethyl-3-cyclopropyl-2-(R),3-(S)-dihydroxypropyl)amino]-3-thiazol-4-yl-propionamide
  参考文献：
  名称：

  Discovery and synthesis of a novel and selective drug-like P2X1 antagonist

  摘要：

  Although there is extensive literature to indicate that many different types of P2 purinoceptors are present in the lower urinary tract, the physiological role of these receptors in micturition is still uncertain. In part, this uncertainty has been caused by a lack of P2 subtype selective ligands. In this paper we report the discovery, gram scale synthesis, and binding results for 1, the first potent, drug-like, selective P2X(1) receptor antagonist described. Compound 1 was shown to be more than 30-fold selective over other purinergic receptor subtypes. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2005.04.049
• 作为产物：
  描述：

  4-cyclohexyl-3-(S)-ethoxycarbonylamino-2-(R)-hydroxybutyric acid 在 氢氧化钾 、 三乙酰氧基硼氢化钠 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正庚烷 、 甲苯 、 乙腈 为溶剂， 反应 24.75h， 生成 (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-butane-1,2-diol
  参考文献：
  名称：

  Discovery and synthesis of a novel and selective drug-like P2X1 antagonist

  摘要：

  Although there is extensive literature to indicate that many different types of P2 purinoceptors are present in the lower urinary tract, the physiological role of these receptors in micturition is still uncertain. In part, this uncertainty has been caused by a lack of P2 subtype selective ligands. In this paper we report the discovery, gram scale synthesis, and binding results for 1, the first potent, drug-like, selective P2X(1) receptor antagonist described. Compound 1 was shown to be more than 30-fold selective over other purinergic receptor subtypes. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2005.04.049

文献信息

• Amino acid derivatives having renin inhibiting activity
  申请人：Hoffmann La Roche Inc.

  公开号：US05688946A1

  公开（公告）日：1997-11-18

  The compounds of the formula ##STR1## in the form of optically pure diastereomers, mixtures of diastereomers, diastereomeric racemates or mixtures of diastereomeric racemates as well as pharmaceutically usable salts thereof inhibit the activity of the natural enzyme renin and can accordingly be used in the form of pharmaceutical preparations in the control or prevention of high blood pressure and cardiac insufficiency.

  上述化学公式##STR1##的化合物，以光学纯的立体异构体、立体异构体混合物、立体异构体对映体混合物或立体异构体对映体混合物的形式，以及它们的药用盐，都能抑制天然酶肾素的活动，因此可以以药物制剂的形式用于控制或预防高血压和心功能不全。
• Amino acid derivatives useful as renin inhibitors
  申请人：Hoffmann-La Roche Inc.

  公开号：US05278161A1

  公开（公告）日：1994-01-11

  Compounds of the formula ##STR1## wherein A, B, X, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as set forth in the specification, in the form of optically pure diastereomers, mixtures of diastereomers, diastereomeric racemates or mixtures of diasteromeric racemates as well as pharmaceutically acceptable salts thereof which inhibit the activity of the natural enzyme renin and are useful in the control or prevention of high blood pressure and cardiac insufficiency are described.

  本文描述了式##STR1##的化合物，其中A、B、X、Y、R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5如规范中所述，以光学纯的对映异构体形式、对映异构体混合物、对映异构体外消旋体或对映异构体外消旋体混合物的形式存在，以及其药学上可接受的盐，这些化合物抑制天然酶肾素的活性，对高血压和心脏衰竭的控制或预防有用。
• Process for producing amides using catalytic amounts of an N-hydroxy
  申请人：Hoffmann-La Roche Inc.

  公开号：US05536816A1

  公开（公告）日：1996-07-16

  A process for the manufacture of amides, including peptides, by reacting a carboxylic acid with a primary or secondary amine in the presence of a carbodiimide and a catalytic amount of a N-hydroxy compound.

  一种制造酰胺（包括肽）的过程，通过在碳二亚胺和一定催化量的N-羟基化合物存在下，将羧酸与一级或二级胺反应。
• Pyrrolopyrazine Kinase Inhibitors
  申请人：Hendricks Robert Than

  公开号：US20110288067A1

  公开（公告）日：2011-11-24

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables Q and R, R 2 , and R 3 are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及使用新型 Formula I 中的吡咯吡嗪衍生物，其中变量 Q 和 R、R2 和 R3 如本文所述定义，这些衍生物抑制 JAK 和 SYK，并用于治疗自身免疫和炎症性疾病。
• PYRROLOPYRAZINE KINASE INHIBITORS
  申请人：Hoffmann-La Roche Inc.

  公开号：US20140155376A1

  公开（公告）日：2014-06-05

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables Q and R, R 2 , and R 3 are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及使用公式I中的新型吡咯吡嗪衍生物，其中变量Q和R，R2和R3的定义如本文所述，它们抑制JAK和SYK，并且对于治疗自身免疫和炎症性疾病是有用的。