2-萘基-2-基-苯并恶唑-5-基-胺 | 95888-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-萘基-2-基-苯并恶唑-5-基-胺
• 英文名称: 2-(naphthalene-2-yl)-benzo[d]oxazole-5-amine
• 英文别名: 2-Naphthalen-2-yl-benzooxazol-5-yl-amine；2-naphthalen-2-yl-1,3-benzoxazol-5-amine
• CAS: 95888-12-3
• 化学式: C₁₇H₁₂N₂O
• mdl: MFCD00423071
• 分子量: 260.295
• InChiKey: YUVSHBCMUZGXKP-UHFFFAOYSA-N

物化性质

• 沸点：
  464.0±18.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-萘基-2-基-苯并恶唑-5-基-胺 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-(2-(naphthalen-2-yl)benzo[d]oxazol-5-yl)isothiazolidine 1,1-dioxide
  参考文献：
  名称：

  2-Arylbenzo[d]oxazole Phosphinate Esters as Second-Generation Modulators of Utrophin for the Treatment of Duchenne Muscular Dystrophy

  摘要：

  Utrophin modulation is a promising therapeutic strategy for Duchenne muscular dystrophy (DMD), which should be applicable to all patient populations. Following on from ezutromid, the first-generation utrophin modulator, we describe the development of a second generation of utrophin modulators, based on the bioisosteric replacement of the sulfone group with a phosphinate ester and substitution of the metabolically labile naphthalene with a haloaryl substituent. The improved physicochemical and absorption, distribution, metabolism, and excretion (ADME) properties, further reflected in the enhanced pharmacokinetic profile of the most advanced compounds, 30 and 27, led to significantly better in vivo exposure compared to ezutromid and alleviation of the dystrophic phenotype in mdx mice. While 30 was found to have dose-limiting hepatotoxicity, 27 and its enantiomers exhibited limited off-target effects, resulting in a safe profile and highlighting their potential utility as next-generation utrophin modulators suitable for progression toward a future DMD therapy.

  DOI：

  10.1021/acs.jmedchem.0c00807
• 作为产物：
  描述：

  2,4-diaminophenol dihydrochloride 、 2-萘甲酸 在 polyphosphoric acid (PPA) 作用下， 以75%的产率得到2-萘基-2-基-苯并恶唑-5-基-胺
  参考文献：
  名称：

  Anticancer supplement agent including benzo[D]oxazol derivative as effective ingredient

  摘要：

  本发明揭示了一种抗癌补充剂，包括苯并[d]噁唑衍生物作为有效成分。苯并[d]噁唑衍生物是核因子E2相关因子2（Nrf2）抑制剂，能够抑制Nrf2活性，从而抑制诱导抗氧化酶清除致癌细胞的活性氧（ROS）的Nrf2活性，增加ROS的产生。因此，苯并[d]噁唑衍生物可用作抗癌补充剂，在抗癌药物治疗或放疗中显示治疗效果，在这方面，苯并[d]噁唑衍生物可以克服癌细胞对抗癌药物治疗或放疗的耐受性，并增强对癌细胞的凋亡作用。

  公开号：

  US09447054B2

文献信息

• ANTICANCER SUPPLEMENT AGENT INCLUDING BENZO[D]OXAZOL DERIVATIVE AS EFFECTIVE INGREDIENT
  申请人：KOREA INSTITUTE OF RADIOLOGICAL & MEDICAL SCIENCES

  公开号：US20150197498A1

  公开（公告）日：2015-07-16

  Disclosed is an anticancer supplement agent including a benzo[d]oxazole derivative as an effective ingredient. The benzo[d]oxazole derivative, which is a nuclear factor E2-related factor 2 (Nrf2) inhibitor, is capable of inhibiting activity of Nrf2 that induces an antioxidant enzyme to remove reactive oxygen species (ROS) that kills a cancer cell, thereby increasing production of ROS. Therefore, the benzo[d]oxazole derivative can be used as an anticancer supplement agent that shows therapeutic effects in anticancer agent therapy or radiation therapy, and in this regard, the benzo[d]oxazole derivative can overcome tolerance of the cancer cell to anticancer agent therapy or radiation therapy and enhance apoptotic effects on the cancer cell.

  本披露了一种抗癌补充剂，其包括一种苯并[d]噁唑衍生物作为有效成分。该苯并[d]噁唑衍生物是一种核因子E2相关因子2（Nrf2）抑制剂，能够抑制Nrf2的活性，从而诱导抗氧化酶去除杀死癌细胞的活性氧自由基（ROS），进而增加ROS的产生。因此，该苯并[d]噁唑衍生物可作为一种抗癌补充剂使用，展现出在抗癌药物治疗或放射治疗中的治疗效果。在这方面，该苯并[d]噁唑衍生物可以克服癌细胞对抗癌药物治疗或放射治疗的耐受性，并增强对癌细胞的凋亡效应。
• Anticancer supplement agent including benzo[D]oxazol derivative as effective ingredient
  申请人：KOREA INSTITUTE OF RADIOLOGICAL & MEDICAL SCIENCES

  公开号：US09447054B2

  公开（公告）日：2016-09-20

  Disclosed is an anticancer supplement agent including a benzo[d]oxazole derivative as an effective ingredient. The benzo[d]oxazole derivative, which is a nuclear factor E2-related factor 2 (Nrf2) inhibitor, is capable of inhibiting activity of Nrf2 that induces an antioxidant enzyme to remove reactive oxygen species (ROS) that kills a cancer cell, thereby increasing production of ROS. Therefore, the benzo[d]oxazole derivative can be used as an anticancer supplement agent that shows therapeutic effects in anticancer agent therapy or radiation therapy, and in this regard, the benzo[d]oxazole derivative can overcome tolerance of the cancer cell to anticancer agent therapy or radiation therapy and enhance apoptotic effects on the cancer cell.

  本发明揭示了一种抗癌补充剂，包括苯并[d]噁唑衍生物作为有效成分。苯并[d]噁唑衍生物是核因子E2相关因子2（Nrf2）抑制剂，能够抑制Nrf2活性，从而抑制诱导抗氧化酶清除致癌细胞的活性氧（ROS）的Nrf2活性，增加ROS的产生。因此，苯并[d]噁唑衍生物可用作抗癌补充剂，在抗癌药物治疗或放疗中显示治疗效果，在这方面，苯并[d]噁唑衍生物可以克服癌细胞对抗癌药物治疗或放疗的耐受性，并增强对癌细胞的凋亡作用。
• [EN] BENZOXAZOLES FOR THE TREATMENT OF DUCHENNE MUSCULAR DYSTROPHY<br/>[FR] BENZOXAZOLES POUR LE TRAITEMENT DE LA DYSTROPHIE MUSCULAIRE DE DUCHENNE
  申请人：BIOMARIN IGA LTD

  公开号：WO2010112093A1

  公开（公告）日：2010-10-07

  Compounds of formula (I), wherein R1, R2, R3, X and n are as defined herein, are useful for the treatment or prophylaxis of conditions such as Duchenne muscular dystrophy, Becker muscular dystrophy, and cachexia.

  化合物公式（I），其中R1，R2，R3，X和n的定义如本文所述，可用于治疗或预防如杜氏肌萎缩症，贝克肌萎缩症和消瘦等疾病。
• Systems pharmacology for treating ocular disorders
  申请人：Case Western Reserve University

  公开号：US10117868B2

  公开（公告）日：2018-11-06

  A method of treating an ocular disorder in a subject includes administering to the subject subtherapeutic amounts of two or more agents that inhibit and/or blocks the activation of Gs- or Gq-protein coupled receptors or Gs- or Gq-signaling cascade in ocular cells of the subject, and/or activates Gi-protein coupled receptors, which is induced or triggered by light induced all-trans-retinal generation.

  一种治疗受试者眼部疾病的方法包括向受试者施用亚治疗量的两种或两种以上抑制和/或阻断受试者眼部细胞中 Gs 或 Gq 蛋白偶联受体或 Gs 或 Gq 信号级联激活的制剂，和/或激活 Gi- 蛋白偶联受体，这是由光诱导全反式视网膜生成诱导或触发的。
• Compounds and methods of treating ocular disorders
  申请人：Case Western Reserve University

  公开号：US10208049B2

  公开（公告）日：2019-02-19

  A method of treating an ocular disorder in a subject associated with aberrant all-trans-retinal clearance in the retina, the method comprising administering to the subject a therapeutically effective amount of a primary amine compound of formula: wherein R1 is an aliphatic and/or aromatic compound.

  一种治疗与视网膜中全反式视网膜清除异常有关的受试者眼部疾病的方法，该方法包括向受试者施用治疗有效量的式伯胺化合物： 其中 R1 是脂肪族和/或芳香族化合物。