N-[(1R)-1-[甲氧基(甲基)氨基甲酰基]乙基]氨基甲酸苄酯 | 152169-60-3

• 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
• 中文名称: N-[(1R)-1-[甲氧基(甲基)氨基甲酰基]乙基]氨基甲酸苄酯
• 英文名称: benzyl {(2R)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate
• 英文别名: [(R)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid benzyl ester；benzyl N-[(1R)-1-[methoxy(methyl)carbamoyl]ethyl]carbamate；benzyl N-[(2R)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate
• CAS: 152169-60-3
• 化学式: C₁₃H₁₈N₂O₄
• 分子量: 266.297
• InChiKey: JJWLCBIYQXRMNO-SNVBAGLBSA-N

物化性质

• 溶解度：
  可溶于氯仿；二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(1R)-1-[甲氧基(甲基)氨基甲酰基]乙基]氨基甲酸苄酯 在 lithium aluminium tetrahydride 、 [VCl3(thf)3] 、 铜 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 dibenzyl ((2R,3S,4S,5R)-3,4-dihydroxyhexane-2,5-diyl)dicarbamate
  参考文献：
  名称：

  Preparation and Structure−Activity Relationship of Novel P1/P1‘-Substituted Cyclic Urea-Based Human Immunodeficiency Virus Type-1 Protease Inhibitors

  摘要：

  A series of novel P1/P1'-substituted cyclic urea-based HIV-1 protease inhibitors was prepared. Three different synthetic schemes were used to assemble these compounds. The first approach uses amino acid-based starting materials and was originally used to prepare DMP 323. The other two approaches use L-tartaric acid or L-mannitol as the starting material. The required four contiguous R,S,S,R centers of the cyclic urea scaffold are introduced using substrate control methodology. Each approach has specific advantages based on the desired P1/P1' substituent. Designing analogs based on the enzyme's natural substrates provided compounds with reduced activity. Attempts at exploiting hydrogen bond sites in the S1/S1' pocket, suggested by molecular modeling studies, were not fruitful. Several analogs had better binding affinity compared to our initial leads. Modulating the compound's physical properties led to a 10-fold improvement in translation resulting in better overall antiviral activity.

  DOI：

  10.1021/jm960083n
• 作为产物：
  描述：

  N-benzyloxycarbonyl-D-alanine 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 N-[(1R)-1-[甲氧基(甲基)氨基甲酰基]乙基]氨基甲酸苄酯
  参考文献：
  名称：

  Preparation and Structure−Activity Relationship of Novel P1/P1‘-Substituted Cyclic Urea-Based Human Immunodeficiency Virus Type-1 Protease Inhibitors

  摘要：

  A series of novel P1/P1'-substituted cyclic urea-based HIV-1 protease inhibitors was prepared. Three different synthetic schemes were used to assemble these compounds. The first approach uses amino acid-based starting materials and was originally used to prepare DMP 323. The other two approaches use L-tartaric acid or L-mannitol as the starting material. The required four contiguous R,S,S,R centers of the cyclic urea scaffold are introduced using substrate control methodology. Each approach has specific advantages based on the desired P1/P1' substituent. Designing analogs based on the enzyme's natural substrates provided compounds with reduced activity. Attempts at exploiting hydrogen bond sites in the S1/S1' pocket, suggested by molecular modeling studies, were not fruitful. Several analogs had better binding affinity compared to our initial leads. Modulating the compound's physical properties led to a 10-fold improvement in translation resulting in better overall antiviral activity.

  DOI：

  10.1021/jm960083n

文献信息

• Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20140128372A1

  公开（公告）日：2014-05-08

  The present application relates to novel substituted imidazo[1,2-a]pyridine-3-carboxamides, to processes for their preparation, to their use alone or in combinations for the treatment and/or prophylaxis of diseases and to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular disorders.

  本申请涉及新型取代咪唑[1,2-a]吡啶-3-羧酰胺，其制备方法，单独或组合使用以治疗和/或预防疾病，以及用于制备治疗和/或预防疾病的药物，特别是用于治疗和/或预防心血管疾病。
• ALPHA 1A-ADRENOCEPTOR ANTAGONISTS
  申请人：Liu Julie F.

  公开号：US20100076010A1

  公开（公告）日：2010-03-25

  This invention relates to novel compounds that are dihydroindoles derivatives and pharmaceutically acceptable salts thereof. More specifically, this invention relates to novel dihydroindoles derivatives that are derivatives of silodosin. This invention also provides compositions comprising one or more compounds of this invention and a carrier and the use of the disclosed compounds and compositions in methods of treating diseases and conditions that are beneficially treated by administering an α-1A-adrenoreceptor antagonist, such as silodosin.

  本发明涉及一种新颖的化合物，它们是二氢吲哚衍生物及其药学上可接受的盐。更具体地说，本发明涉及一种新颖的二氢吲哚衍生物，它们是硅唑洛辛的衍生物。本发明还提供了包含本发明中的一种或多种化合物和载体的组合物，以及使用所披露的化合物和组合物治疗通过给予α-1A-肾上腺素受体拮抗剂（如硅唑洛辛）有益治疗的疾病和病状的方法。
• CYCLIC DIARYL ETHER COMPOUNDS AS ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS
  申请人：Hutchinson John Howard

  公开号：US20110098302A1

  公开（公告）日：2011-04-28

  Described herein are compounds that are antagonists of PGD 2 receptors. Also described are pharmaceutical compositions and medicaments that include the antagonists of PGD 2 receptors described herein, as well as methods of using such antagonists of PGD 2 receptors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other PGD 2 -dependent or PGD 2 -mediated conditions or diseases.

  本文描述了PGD2受体拮抗剂化合物。还描述了包括本文所述的PGD2受体拮抗剂在内的制药组合物和药物，以及使用这种PGD2受体拮抗剂，单独或与其他化合物结合，治疗呼吸系统、心血管系统和其他PGD2依赖性或PGD2介导的疾病或病症的方法。
• AMINO-SUBSTITUTED IMIDAZO[1,2-A]PYRIDINECARBOXAMIDES AND THEIR USE
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20150274719A1

  公开（公告）日：2015-10-01

  The present application relates to novel substituted imidazo[1,2-a]pyridine-3-carboxamides, to processes for their preparation, to their use alone or in combinations for the treatment and/or prophylaxis of diseases and to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular disorders.

  本申请涉及新型取代的咪唑并[1,2-a]吡啶-3-羧酰胺，其制备方法，其单独或与其他药物联合用于治疗和/或预防疾病，以及其用于制备治疗和/或预防疾病的药物，特别是用于治疗和/或预防心血管疾病。
• 一种西洛多辛手性中间体的制备方法
  申请人：中山大学

  公开号：CN107857720A

  公开（公告）日：2018-03-30

  本发明提供一种合成高对映纯度的西洛多辛中间体的方法。该方法以1‑[3‑(苄氧基)丙基]‑5‑溴‑吲哚啉为原料，与有机锂试剂进行溴锂交换反应，得到1‑[3‑(苄氧基)丙基]‑5‑锂‑吲哚啉，再与(R)‑N‑烷氧羰基‑丙氨酸Weinreb酰胺反应，以良好的产率和对映选择性得到西洛多辛中间体。该方法操作简单，原料廉价易得，产物对映纯度高，无需拆分步骤，对于西洛多辛的工业制备具有很高的应用价值。