(2R,3S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid | 80542-17-2

• 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
• 英文名称: (2R,3S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid
• 英文别名: (R,S)-A-N-Boc-amino-B-hydroxy-cyclohexanepropanic acid；(2R,3S)-3-cyclohexyl-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 80542-17-2
• 化学式: C₁₄H₂₅NO₅
• 分子量: 287.356
• InChiKey: KOKGNBSMQYDZSC-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid 在 20 % Pd(OH)2/C 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 50.0~80.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 (3R)-1-butyl-3-[(S)-cyclohexyl(hydroxy)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione;hydrochloride
  参考文献：
  名称：

  Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: A highly potent orally available CCR5 selective antagonist

  摘要：

  Based on the original spirodiketopiperazine design framework, further optimization of an orally available CCR5 antagonist was undertaken. Structural hybridization of the hydroxylated analog 4 derived from one of the oxidative metabolites and the new orally available non-hydroxylated benzoic acid analog 5 resulted in another potent orally available CCR5 antagonist 6a as a clinical candidate. Full details of a structure-activity relationship (SAR) study and ADME properties are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.022
• 作为产物：
  描述：

  3-cyclohexylacrylic acid 在 叔丁基过氧化氢 、 Jones reagent 、 L-(+)-酒石酸二乙酯 、 硫酸 、 20 % Pd(OH)2/C 、 titanium(IV) isopropoxide 、 氢气 、 sodium hydride 、 二异丁基氢化铝 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正辛烷 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 33.5h， 生成 (2R,3S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid
  参考文献：
  名称：

  Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: A highly potent orally available CCR5 selective antagonist

  摘要：

  Based on the original spirodiketopiperazine design framework, further optimization of an orally available CCR5 antagonist was undertaken. Structural hybridization of the hydroxylated analog 4 derived from one of the oxidative metabolites and the new orally available non-hydroxylated benzoic acid analog 5 resulted in another potent orally available CCR5 antagonist 6a as a clinical candidate. Full details of a structure-activity relationship (SAR) study and ADME properties are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.022

文献信息

• Drugs containing triazaspiro[5.5]undecane derivatives as the active ingredient
  申请人：——

  公开号：US20040106619A1

  公开（公告）日：2004-06-03

  A pharmaceutical composition for prevention and/or treatment for HIV infection or AIDS induced by the infection which comprises, as an active ingredient, a triazaspiro[5.5]undecane derivative, a quaternary ammonium salt thereof, an N-oxide thereof, or a non-toxic salt thereof, and if necessary, it may be combined with at least one member of other agents for prevention and/or treatment for HIV infection (wherein all symbols are as defined in the specification.). 1 The triazaspiro[5.5]undecane derivatives, the quaternary ammonium salts thereof or the N-oxides thereof, or the non-toxic salts thereof are useful in preventing and/or treating HIV infection and AIDS induced by the infection.

  一种用于预防和/或治疗由HIV感染引起的艾滋病的药物组合物，其作为活性成分包括三氮杂螺[5.5]十一烷衍生物、其季铵盐、其N-氧化物或其非毒性盐，如有必要，还可以与其他预防和/或治疗HIV感染的药物组合使用（其中所有符号均如规范中定义） 。1三氮杂螺[5.5]十一烷衍生物、其季铵盐或其N-氧化物，或其非毒性盐在预防和/或治疗HIV感染和由该感染引起的艾滋病中有用。
• DRUGS CONTAINING TRIAZASPIRO 5.5]UNDECANE DERIVATIVES AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1378509A1

  公开（公告）日：2004-01-07

  A pharmaceutical composition for prevention and/or treatment for HIV infection or AIDS induced by the infection which comprises, as an active ingredient, a triazaspiro[5.5]undecane derivative, a quaternary ammonium salt thereof, an N-oxide thereof, or a non-toxic salt thereof, and if necessary, it may be combined with at least one member of other agents for prevention and/or treatment for HIV infection (wherein all symbols are as defined in the specification.). The triazaspiro[5.5]undecane derivatives, the quatemary ammonium salts thereof or the N-oxides thereof, or the non-toxic salts thereof are useful in preventing and/or treating HIV infection and AIDS induced by the infection.

  一种用于预防和/或治疗HIV感染或由该感染诱发的艾滋病的药物组合物，作为活性成分，它包括一种三氮杂螺[5.5]十一烷衍生物、其季铵盐、其N-氧化物或其无毒盐，必要时，它可与至少一种用于预防和/或治疗HIV感染的其他制剂成员结合使用（其中所有符号如说明书中所定义。） 三氮杂螺[5.5]十一烷衍生物、其藜芦铵盐或其N-氧化物或其无毒盐可用于预防和/或治疗HIV感染和由感染诱发的艾滋病。
• Triazaspiro[5.5]undecane derivatives and drugs containing the same as the active ingredient
  申请人：——

  公开号：US20040097511A1

  公开（公告）日：2004-05-20

  Triazaspiro[5.5]undecane derivatives, quaternary ammonium salts thereof, N-oxides thereof, non-toxic salts thereof, or pharmaceutical compositions comprising them, as an active ingredient. 1 So the compounds of the formula (I) regulate the effect of chemokine/chemokine receptor, they are used for prevention and treatment of various inflammatory diseases, asthma, atopic dermatitis, urticaria, allergic diseases, nephritis, nephropathy, hepatitis, arthritis or rheumatoid arthritis etc.

  作为活性成分的三氮杂螺[5.5]十一烷衍生物、其季铵盐、其 N-氧化物、其无毒盐或包含它们的药物组合物。 1 因此，式（I）化合物具有调节趋化因子/趋化因子受体的作用，可用于预防和治疗各种炎症性疾病、哮喘、特应性皮炎、荨麻疹、过敏性疾病、肾炎、肾病、肝炎、关节炎或类风湿性关节炎等。
• TRIAZASPIRO 5.5]UNDECANE DERIVATIVES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1236726B1

  公开（公告）日：2004-12-01
• US7119091B2
  申请人：——

  公开号：US7119091B2

  公开（公告）日：2006-10-10