N-(4-ethylphenyl)benzo[d]oxazole-2,5-diamine | 1352429-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: N-(4-ethylphenyl)benzo[d]oxazole-2,5-diamine
• 英文别名: N²-(4-ethylphenyl)benzo[d]oxazole-2,5-diamine；N2-(4-ethylphenyl)benzo[d]oxazole-2,5-diamine；2-N-(4-ethylphenyl)-1,3-benzoxazole-2,5-diamine
• CAS: 1352429-18-5
• 化学式: C₁₅H₁₅N₃O
• 分子量: 253.304
• InChiKey: HMUSVHZYELITJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-ethylphenyl)benzo[d]oxazole-2,5-diamine 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 5-(4-cyanophenoxy)-N-(2-(4-ethylphenylamino)benzo[d]oxazol-5-yl)pentanamide
  参考文献：
  名称：

  신규한 화합물, 이의 제조방법 및 이를 포함하는 골다공증 완화, 예방 또는 치료용 약학조성물

  摘要：

  本发明提供了以下[化学式I]的新化合物，其药学上可接受的盐，或其水合物或溶剂化合物，以及其制备方法和含有效量的治疗骨质疏松症的缓解、预防或治疗组合物。[化学式I]

  公开号：

  KR101857141B1
• 作为产物：
  描述：

  2-氨基-4-硝基苯酚 在 potassium superoxide 、 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 64.0h， 生成 N-(4-ethylphenyl)benzo[d]oxazole-2,5-diamine
  参考文献：
  名称：

  合成作为白介素6拮抗剂的苯并恶唑衍生物。

  摘要：

  越来越多的研究表明，白细胞介素（IL）-6通过激活先天免疫细胞并刺激适应性T细胞，在慢性炎症和自身免疫性疾病的发展中发挥病理作用。因此，抑制IL-6功能可能对预防和治疗慢性炎性疾病有益。这项研究报告说，苯并恶唑的一系列合成衍生物对IL-6介导的信号传导具有抑制作用。在苯并恶唑的16种合成衍生物中，化合物4、6、11、15、17和19显示出对IL-6诱导的信号转导子和转录激活子（STAT）3磷酸化的强抑制活性，为80-90％。尽管化合物11、17、19大大降低了细胞活力，但化合物4、6和15却显示出较低的细胞毒性。然后，我们检查了这些化合物对CD4 + T细胞产生炎性细胞因子的影响。在化合物4或化合物7存在下，诱导CD4 + T细胞分化为产生干扰素（IFN）-γ-，IL-17-或IL-4的效应T细胞，而无活性的化合物7没有对效应T细胞产生的细胞因子产生显着影响，活性化合物4强烈抑制炎症细胞因

  DOI：

  10.1016/j.bmc.2017.03.072

文献信息

• Benzoxazole Derivatives Having Inhibitory Activity Against Interleukin-6, Preparation Method Thereof, and Pharmaceutical Composition Containing the Same
  申请人：Park Choo Hea Young

  公开号：US20130090480A1

  公开（公告）日：2013-04-11

  The present invention relates to benzoxazole derivatives represented by the Formula 1, which has an inhibitory activity against interleukin-6 (IL-6), a method for preparation thereof, and a pharmaceutical composition containing the same. The compound represented by the Formula 1 according to the present invention has a superior inhibitory activity against interleukin-6, and therefore, can be practically applied for prevention and treatment of diseases caused by abnormal interleukin-6 activity.

  本发明涉及由公式1表示的苯并噁唑衍生物，其具有对白细胞介素-6（IL-6）的抑制活性，以及其制备方法和含有该化合物的药物组合物。根据本发明的公式1所表示的化合物具有优越的抑制白细胞介素-6的活性，因此，可以实际应用于预防和治疗由异常白细胞介素-6活性引起的疾病。
• Benzoxazole derivatives having inhibitory activity against interleukin-6, preparation method thereof, and pharmaceutical composition containing the same
  申请人：Park Choo Hea Young

  公开号：US08614240B2

  公开（公告）日：2013-12-24

  The present invention relates to benzoxazole derivatives represented by the Formula 1, which has an inhibitory activity against interleukin-6 (IL-6), a method for preparation thereof, and a pharmaceutical composition containing the same. The compound represented by the Formula 1 according to the present invention has a superior inhibitory activity against interleukin-6, and therefore, can be practically applied for prevention and treatment of diseases caused by abnormal interleukin-6 activity.

  本发明涉及一种由公式1表示的苯并噁唑衍生物，其具有抑制白细胞介素-6（IL-6）的活性，一种其制备方法以及包含该化合物的制药组合物。根据本发明的公式1所表示的化合物具有出色的抑制白细胞介素-6的活性，因此，可以实际应用于预防和治疗由于异常白细胞介素-6活性引起的疾病。
• Novel Small Molecule Inhibitors Targeting the IL-6/STAT3 Pathway or IL-1β
  作者：Jihye Yoo、Darong Kim、Jiyoung Park、Young-Kook Kim、Hea-Young Park Choo、Hyun Ae Woo

  DOI：10.3390/molecules27092696

  日期：——

  Development of small molecules that inhibit inflammatory cytokines is a desirable strategy for the treatment of inflammatory diseases such as rheumatoid arthritis (RA). Following up a previous study, we synthesized 10 novel compounds with a 2,5-diaminobenzoxazole moiety and evaluated their biological activities. Among them, compound 3e showed potent inhibitory activity on Interleukin 6 (IL-6)/Signal Transducer and Activator of Transcription 3 (STAT3) signaling inhibition (71.5%), and 3a showed excellent inhibitory activity on Interleukin 1 (IL-1β) (92.1%). To test in vivo anti-inflammatory activity, compounds 3a and 3e were administered by intraperitoneal (IP) injection after subcutaneous (SC) injection of zymosan A into the right footpad of mice. Inflammation on the footpad was reduced after administration of compounds 3a and 3e. Especially, compound 3a showed a significant ameliorative effect on zymosan-induced inflammation. From the in vivo and in vitro test results, we confirmed that our synthesized compounds are effective on the RA animal model through inhibition of the IL-6/STAT3 signaling pathway. Since drugs developed with small molecule inhibitors have several advantages over biological drugs, further study on these compounds is needed for the development of potent SMI drugs on RA.

  开发能够抑制炎性细胞因子的小分子化合物是治疗类风湿性关节炎等炎性疾病的理想策略。在之前的研究基础上，我们合成了10个新的化合物，其中含有2,5-二氨基苯并咪唑基团，并评估了它们的生物活性。其中，化合物3e在白细胞介素6（IL-6）/信号转导和转录激活子3（STAT3）信号抑制方面表现出强烈的抑制活性（71.5％），而3a在白细胞介素1（IL-1β）方面表现出优异的抑制活性（92.1％）。为了测试体内的抗炎活性，将化合物3a和3e通过腹腔注射给小鼠，然后在小鼠的右脚趾下皮下注射半乳糖神经酰胺A。化合物3a和3e的给药后，足底的炎症得到了减轻。特别是，化合物3a对半乳糖神经酰胺A诱导的炎症具有显著的改善作用。通过体内和体外实验结果，我们确认我们合成的化合物通过抑制IL-6 / STAT3信号通路对类风湿性关节炎动物模型具有有效性。由于使用小分子抑制剂开发的药物具有多种优势，因此需要进一步研究这些化合物，以开发出对类风湿性关节炎具有强效作用的小分子抑制剂药物。
• [EN] COMPOSITION FOR PREVENTING OR TREATING CHRONIC KIDNEY DISEASE, COMPRISING COMPOUND THAT INDUCES EXPRESSION OF ANTI-AGING GENE KLOTHO<br/>[FR] COMPOSITION POUR PRÉVENIR OU TRAITER UNE MALADIE RÉNALE CHRONIQUE, COMPRENANT UN COMPOSÉ QUI INDUIT L'EXPRESSION D'UN GÈNE KLOTHO ANTI-VIEILLISSEMENT<br/>[KO] 항노화 유전자 KLOTHO의 발현을 유도하는 화합물을 포함하는 만성신장질환의 예방 또는 치료용 조성물
  申请人：KLOTHO SCIENCES

  公开号：WO2022211574A1

  公开（公告）日：2022-10-06

  본 발명은 항노화 유전자 klotho의 발현을 유도하는 화합물을 포함하는 만성신장질환((chronic kidney disease, CKD)의 예방 또는 치료용 조성물에 관한 것이다. 본 발명에 따른 화학식 1로 표시되는 화합물은 노화와 관련된 유전자인 Klotho 유전자의 발현량을 향상시키는 효과가 우수하며, 만성신장질환의 예방, 개선 또는 치료용 약학 조성물 또는 식품 조성물로 유용하게 사용될 수 있다.

  本发明涉及含有诱导抗衰老基因klotho表达的化合物的慢性肾脏疾病（CKD）预防或治疗配方。根据本发明，用化学式1表示的化合物具有优异的增强与衰老相关的基因Klotho基因表达量的效果，可用作预防、改善或治疗慢性肾脏疾病的药物配方或食品配方。
• 5-Lipoxygenase inhibitors suppress RANKL-induced osteoclast formation via NFATc1 expression
  作者：Ju-Hee Kang、Zheng Ting、Mi-ran Moon、Jung-Seon Sim、Jung-Min Lee、Kyung-Eun Doh、Sunhye Hong、Minghua Cui、Sun Choi、Hyeun Wook Chang、Hea-Young Park Choo、Mijung Yim

  DOI：10.1016/j.bmc.2015.09.025

  日期：2015.11

  5-Lipoxygenase synthesizes leukotrienes from arachidonic acid. We developed three novel 5-LO inhibitors having a benzoxazole scaffold as a potential anti-osteoclastogenics. They significantly suppressed RANKL-induced osteoclast formation in mouse bone marrow-derived macrophages. Furthermore, one compound, K7, inhibited the bone resorptive activity of osteoclasts. The anti-osteoclastogenic effect of K7 was mainly attributable to reduction in the expression of NFATc1, an essential transcription factor for osteoclast differentiation. K7 inhibited osteoclast formation via ERR and p38 MAPK, as well as NF-kappa B signaling pathways. K7 reduced lipopolysaccharide (LPS)-induced osteoclast formation in vivo, corroborating the in vitro data. Thus, K7 exerted an inhibitory effect on osteoclast formation in vitro and in vivo, properties that make it a potential candidate for the treatment of bone diseases associated with excessive bone resorption. (C) 2015 Elsevier Ltd. All rights reserved.