(4-丙基苯基)甲胺盐酸盐 | 856627-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-丙基苯基)甲胺盐酸盐
• 英文名称: N-benzyl-N-methylethane-1,2-diamine dihydrochloride
• 英文别名: (4-propylphenyl)methanamine hydrochloride；(4-Propylphenyl)methanamine hydrochloride；(4-propylphenyl)methanamine;hydrochloride
• CAS: 856627-23-1
• 化学式: C₁₀H₁₅N*ClH
• 分子量: 185.697
• InChiKey: YROYVCIXPCLPMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2921499090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-苯并唑啉酮 、 三光气 、 (4-丙基苯基)甲胺盐酸盐 在 吡啶 作用下， 反应 3.5h， 以29%的产率得到2-oxo-N-[(4-propylphenyl)methyl]-1,3-benzoxazole-3-carboxamide
  参考文献：
  名称：

  Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure–Activity Relationship (SAR) Studies

  摘要：

  Ceramides are lipid-derived intracellular messengers involved in the control of senescence, inflammation, and apoptosis. The cysteine amidase, acid ceramidase (AC), hydrolyzes these substances into sphingosine and fatty acid and, by doing so, regulates their signaling activity. AC inhibitors may be useful in the treatment of pathological conditions, such as cancer, in which ceramide levels are abnormally reduced. Here, we present a systematic SAR investigation of the benzoxazolone carboxamides, a recently described class of AC inhibitors that display high potency and systemic activity in mice. We examined a diverse series of substitutions on both benzoxazolone ring and carboxamide side chain. Several modifications enhanced potency and stability, and one key compound with a balanced activity stability profile (14) was found to inhibit AC activity in mouse lungs and cerebral cortex after systemic administration. The results expand our arsenal of AC inhibitors, thereby facilitating the use of these compounds as pharmacological tools and their potential development as drug leads.

  DOI：

  10.1021/acs.jmedchem.5b01188

文献信息

• [EN] BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS<br/>[FR] DÉRIVÉS DE BENZOXAZOLONE EN TANT QU'INHIBITEURS DE LA CÉRAMIDASE ACIDE, ET LEUR UTILISATION COMME MÉDICAMENTS
  申请人：FOND ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：WO2015173168A1

  公开（公告）日：2015-11-19

  The present invention relates to benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides benzoxazolone derivatives for use as a medicament in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

  本发明涉及苯并噁唑酮衍生物作为酸酶抑制剂，含有这些抑制剂的药物组合物以及用于抑制酸酶治疗临床相关的调节神经酰胺水平的疾病的方法。该发明还提供苯并噁唑酮衍生物作为药物在治疗癌症、炎症、疼痛、炎症性疼痛或肺部疾病中的用途。
• Benzoxazolone derivatives as acid ceramidase inhibitors, and their use as medicaments
  申请人：FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：US10226452B2

  公开（公告）日：2019-03-12

  The present invention relates to benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides benzoxazolone derivatives for use as a medicament in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

  本发明涉及作为酸性神经酰胺酶抑制剂的苯并恶唑酮衍生物、含有这些抑制剂的药物组合物和抑制酸性神经酰胺酶的方法，用于治疗神经酰胺水平的调节与临床相关的疾病。本发明还提供了用作治疗癌症、炎症、疼痛、炎性疼痛或肺部疾病的药物的苯并恶唑酮衍生物。
• BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS
  申请人：FONDAZIONE ISTITUTO ITALIANO DI TECHOLOGIA

  公开号：US20170182010A1

  公开（公告）日：2017-06-29

  The present invention relates to benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides benzoxazolone derivatives for use as a medicament in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.
• Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure–Activity Relationship (SAR) Studies
  作者：Anders Bach、Daniela Pizzirani、Natalia Realini、Valentina Vozella、Debora Russo、Ilaria Penna、Laurin Melzig、Rita Scarpelli、Daniele Piomelli

  DOI：10.1021/acs.jmedchem.5b01188

  日期：2015.12.10

  Ceramides are lipid-derived intracellular messengers involved in the control of senescence, inflammation, and apoptosis. The cysteine amidase, acid ceramidase (AC), hydrolyzes these substances into sphingosine and fatty acid and, by doing so, regulates their signaling activity. AC inhibitors may be useful in the treatment of pathological conditions, such as cancer, in which ceramide levels are abnormally reduced. Here, we present a systematic SAR investigation of the benzoxazolone carboxamides, a recently described class of AC inhibitors that display high potency and systemic activity in mice. We examined a diverse series of substitutions on both benzoxazolone ring and carboxamide side chain. Several modifications enhanced potency and stability, and one key compound with a balanced activity stability profile (14) was found to inhibit AC activity in mouse lungs and cerebral cortex after systemic administration. The results expand our arsenal of AC inhibitors, thereby facilitating the use of these compounds as pharmacological tools and their potential development as drug leads.