(S)-(1-cyclopentyl-pyrrolidine-3-yl)carbamic acid tert-butyl ester | 937397-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-(1-cyclopentyl-pyrrolidine-3-yl)carbamic acid tert-butyl ester
• 英文别名: (1-cyclopentyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester；(S)-tert-Butyl 1-cyclopentylpyrrolidin-3-ylcarbamate；tert-butyl N-[(3S)-1-cyclopentylpyrrolidin-3-yl]carbamate
• CAS: 937397-21-2
• 化学式: C₁₄H₂₆N₂O₂
• 分子量: 254.373
• InChiKey: VFOIOFJINUUTMG-NSHDSACASA-N

物化性质

• 沸点：
  356.1±31.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(1-cyclopentyl-pyrrolidine-3-yl)carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3S)-1-cyclopentylpyrrolidin-3-amine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Naphthamides as Dopamine D₃ Receptor Ligands

  摘要：

  A series of naphthamides were synthesized, and the affinities of these compounds were determined for dopamine D-2 and D-3 receptors using radioligand binding techniques. The naphthamide compounds that were prepared include N-(1-alkylpiperidin-4-yl)-4-bromo-1-methoxy-2-naphthamides (1-6), (S)-N-(1-alkylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamides (7-12), (R)-N-(1-alkylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamides (13-18), (S)-N-(1-alkyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamides (19 -25), (R)-N-(1-alkyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamides (26-31), and N-(9-alkyl-9-azabicyclo-[3.3.1]nonan-3 beta -yl)-4- bromo-1-methoxy-2-naphthamides (32, 33). The results of in vitro radioligand binding studies indicated that the majority of the naphthamide analogues bound with high affinity at both the D-2 and D-3 dopamine receptor subtypes and most of the compounds demonstrated some selectivity for the dopamine D-3 dopamine receptor subtype. These results demonstrated that both the structure of the central amine moiety (piperidine, pyrrolidine, and 9-azabicyclo[3.3.1]nonane) ring and the N-(alkyl) substitution on the amine significantly effects the binding affinity at D-2 and D-3 dopamine receptors. The bulkiness of the N-(1-alkyl) substituent was found to (a) have no effect on pharmacologic selectivity, (b) increase the affinity at Ds receptors, or (c) decrease the affinity at D-2 receptors. The most potent analogue in this series was (S)-N-(1-cycloheptylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamide (10), which had equilibrium dissociation (K-i) values of 1.8 and 0.2 nM for D-2 and D-3 receptors, respectively. The most selective analogue was (R)-N-(1-cycloheptyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamide (30), which had K-i values of 62.8 and 2.4 nM for D-2 and D-3 receptors, respectively. Radioligand binding results for sigma receptors indicated that the structure of the amine moiety and the N-(l-alkyl) substitutions also significantly influence the affinity and selectivity of these compounds at the sigma (1) and sigma (2) sigma receptor subtypes. The two naphthamides containing a 9-azabicyclo[3.3.1]nonan-3 beta -yl central ring were found to be selective for sigma (2) receptors.

  DOI：

  10.1021/jm0100077
• 作为产物：
  描述：

  环戊酮 、 (S)-(-)-1-苄基-3-(叔丁氧羰基氨基)吡咯烷 在 5percent Pd/C 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (S)-(1-cyclopentyl-pyrrolidine-3-yl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Naphthamides as Dopamine D₃ Receptor Ligands

  摘要：

  A series of naphthamides were synthesized, and the affinities of these compounds were determined for dopamine D-2 and D-3 receptors using radioligand binding techniques. The naphthamide compounds that were prepared include N-(1-alkylpiperidin-4-yl)-4-bromo-1-methoxy-2-naphthamides (1-6), (S)-N-(1-alkylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamides (7-12), (R)-N-(1-alkylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamides (13-18), (S)-N-(1-alkyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamides (19 -25), (R)-N-(1-alkyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamides (26-31), and N-(9-alkyl-9-azabicyclo-[3.3.1]nonan-3 beta -yl)-4- bromo-1-methoxy-2-naphthamides (32, 33). The results of in vitro radioligand binding studies indicated that the majority of the naphthamide analogues bound with high affinity at both the D-2 and D-3 dopamine receptor subtypes and most of the compounds demonstrated some selectivity for the dopamine D-3 dopamine receptor subtype. These results demonstrated that both the structure of the central amine moiety (piperidine, pyrrolidine, and 9-azabicyclo[3.3.1]nonane) ring and the N-(alkyl) substitution on the amine significantly effects the binding affinity at D-2 and D-3 dopamine receptors. The bulkiness of the N-(1-alkyl) substituent was found to (a) have no effect on pharmacologic selectivity, (b) increase the affinity at Ds receptors, or (c) decrease the affinity at D-2 receptors. The most potent analogue in this series was (S)-N-(1-cycloheptylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamide (10), which had equilibrium dissociation (K-i) values of 1.8 and 0.2 nM for D-2 and D-3 receptors, respectively. The most selective analogue was (R)-N-(1-cycloheptyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamide (30), which had K-i values of 62.8 and 2.4 nM for D-2 and D-3 receptors, respectively. Radioligand binding results for sigma receptors indicated that the structure of the amine moiety and the N-(l-alkyl) substitutions also significantly influence the affinity and selectivity of these compounds at the sigma (1) and sigma (2) sigma receptor subtypes. The two naphthamides containing a 9-azabicyclo[3.3.1]nonan-3 beta -yl central ring were found to be selective for sigma (2) receptors.

  DOI：

  10.1021/jm0100077

文献信息

• Pteridinone derivatives as PI3-kinases inhibitors
  申请人：Boehringer Ingelheim Pharma GmbH & Co. KG

  公开号：EP1953163A1

  公开（公告）日：2008-08-06

  New compounds of formula 1 are provided which by virtue of their pharmaceutical activity as PI3-kinase modulators may be used in the therapeutic field for the treatment of inflammatory or allergic diseases. Examples of these include inflammatory and allergic respiratory complaints, inflammatory diseases of the gastro-intestinal tract and motor apparatus, inflammatory and allergic skin diseases, inflammatory eye diseases, diseases of the nasal mucosa, inflammatory or allergic conditions involving autoimmune reactions or inflammations of the kidney.

  根据其作为PI3-激酶调节剂的药理活性，提供了公式1的新化合物，可用于治疗炎症或过敏性疾病的治疗领域。 这些例子包括炎症和过敏性呼吸道疾病，胃肠道和运动器官的炎症性疾病，炎症性和过敏性皮肤疾病，炎症性眼病，鼻黏膜疾病，涉及自身免疫反应或肾脏炎症的炎症性或过敏性疾病。
• Aminophenylsulfonamide Derivatives as Hiv Protease Inhibitor
  申请人：De Kock Herman Augustinus

  公开号：US20080306061A1

  公开（公告）日：2008-12-11

  The present invention concerns substituted aminophenylsulfonamide compounds and derivatives, their use as protease inhibitors, in particular as broadspectrum HIV protease inhibitors, processes for their preparation as well as pharmaceutical compositions and diagnostic kits comprising them. The present invention also concerns combinations of the present substituted aminophenylsulfonamide compounds and derivatives with another anti-retroviral agent. It further relates to their use in assays as reference compounds or as reagents.

  本发明涉及取代的氨基苯磺酰胺化合物及其衍生物，它们的用途为蛋白酶抑制剂，特别是作为广谱HIV蛋白酶抑制剂，以及它们的制备方法、制药组合物和诊断试剂盒。本发明还涉及本发明的取代氨基苯磺酰胺化合物和衍生物与另一种抗逆转录病毒药物的组合。它进一步涉及它们作为参考化合物或试剂在检测中的使用。
• PTERIDINONE DERIVATIVES AS P13-KINASES INHIBITORS
  申请人：Giovannini Riccardo

  公开号：US20100099680A1

  公开（公告）日：2010-04-22

  New compounds of Formula (1) are provided which by virtue of their pharmaceutical activity as PI3-kinase modulators may be used in the therapeutic field for the treatment of inflammatory or allergic diseases. Examples of these include inflammatory and allergic respiratory complaints, inflammatory diseases of the gastro-intestinal tract and motor apparatus, inflammatory and allergic skin diseases, inflammatory eye diseases, diseases of the nasal mucosa, inflammatory or allergic conditions involving autoimmune reactions or inflammations of the kidney.

  提供了Formula（1）的新化合物，由于其作为PI3-kinase调节剂的药理活性，可用于治疗炎症或过敏性疾病的治疗领域。其中包括炎症和过敏性呼吸道疾病，胃肠道和运动器官的炎症性疾病，炎症和过敏性皮肤疾病，炎症性眼部疾病，鼻黏膜疾病，涉及自身免疫反应或肾脏炎症的炎症或过敏性疾病。
• WO2007/60249
  申请人：——

  公开号：——

  公开（公告）日：——
• AMINOPHENYLSULFONAMIDE DERIVATIVES AS HIV PROTEASE INHIBITOR
  申请人：Janssen Sciences Ireland UC

  公开号：EP1960381B1

  公开（公告）日：2015-06-17