(S)-(-)-1-(3-甲氧基苯基)乙基 异氰酸酯 | 745784-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (S)-(-)-1-(3-甲氧基苯基)乙基 异氰酸酯
• 中文别名: (S)-(-)-1-(3-甲氧基苯基)乙基异氰酸酯
• 英文名称: 1-[(1S)-1-isocyanatoethyl]-3-methoxy-benzene
• 英文别名: (S)-(-)-1-(3-Methoxyphenyl)ethyl isocyanate；1-[(1S)-1-isocyanatoethyl]-3-methoxybenzene
• CAS: 745784-08-1
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: YNWCQMWZIOMQOP-QMMMGPOBSA-N

物化性质

• 沸点：
  253.4±33.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  按规定使用和贮存的情况下不会分解。应避免接触氧化物、热量、水分、酒精及胺类物质。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  6.1
• 海关编码：
  2929109000
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  UN2206

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-(3-甲氧基苯基)乙基 异氰酸酯 、 6-氨基-1,4-二氢-4-氧代-2-喹啉羧酸甲酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl 6-[[(1S)-1-(3-methoxyphenyl)ethyl]carbamoylamino]-4-oxo-1H-quinoline-2-carboxylate
  参考文献：
  名称：

  Novel vitexin-inspired scaffold against leukemia

  摘要：

  Acute lymphoblastic leukemia (ALL) is the most common type of leukemia in children. Up to a quarter of ALL patients relapse and face poor prognosis. To identify new compound leads, we conducted a phenotypic screen using terrestrial natural product (NP) fractions against immortalized ALL cellular models.We identified vitexin, a flavonoid, as a promising hit with biological activity (EC50 = 30 mu M) in pre-B cell ALL models with no toxicity against normal human tissue (BJ cells) at the tested concentrations. To develop more potent compounds against ALL and elucidate its potential mode of action, a vitexin-inspired compound library was synthesized. Thus, we developed an improved and scalable protocol for the direct synthesis of 4-quinolone core heterocycles containing an N-sulfonamide using a one-pot condensation reaction protocol. The newly generated compounds represent a novel molecular scaffold against ALL as exemplified by compounds 13 and 15, which demonstrated EC50 values in the low micromolar range (0.3-10 mu M) with little to no toxicity in normal cellular models. Computational studies support the hypothesis that these compounds are potential CDK inhibitors. The compounds induced apoptosis, caused cell arrest at G0/G1 and G2/M, and induced ROS in cancer cells. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.01.004

文献信息

• [EN] NOVEL 4-(AZACYCLOALKYL)BENZENE-1,3-DIOL COMPOUNDS AS TYROSINASE INHIBITORS, PROCESS FOR THE PREPARATION THEREOF AND USE THEREOF IN HUMAN MEDICINE AND IN COSMETICS<br/>[FR] NOUVEAUX COMPOSÉS DE 4- (AZACYCLOALKYL) BENZENE-1, 3-DIOL UTILISÉS COMME INHIBITEURS DE LA TYROSINASE, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR UTILISATION EN MÉDICINE HUMAINE ET DANS LES COSMÉTIQUES
  申请人：GALDERMA RES & DEV

  公开号：WO2010063774A1

  公开（公告）日：2010-06-10

  The present invention relates to novel 4- (azacycloalkyl) benzene-1, 3-diol compounds corresponding to general formula (I) below: Formula (I) to the compositions containing same, to the process for the preparation thereof and to the use thereof in pharmaceutical or cosmetic compositions for use in the treatment or prevention of pigmentary disorders.

  本发明涉及与下面的一般式（I）相对应的新型4-(氮杂环烷基)苯-1,3-二酚化合物：式（I），以及含有这些化合物的组合物，其制备方法以及在制备用于治疗或预防色素紊乱的药用或化妆品组合物中的使用。
• [EN] TRPM8 ANTAGONISTS AND THEIR USE IN TREATMENTS<br/>[FR] ANTAGONISTES DE TRPM8 ET LEUR UTILISATION DANS LE CADRE THÉRAPEUTIQUE
  申请人：AMGEN INC

  公开号：WO2012177896A1

  公开（公告）日：2012-12-27

  Compounds of Formula (I) are useful as antagonists of TRPM8. Such compounds are useful in treating a number of TRPM8 mediated disorders and conditions and may be used to prepare medicaments and pharmaceutical compositions useful for treating such disorders and conditions. Examples of such disorders include, but are not limited to, migraines and neuropathic pain. Compounds of Formula (I) have the above structure, where the definitions of the variables are provided herein.

  式（I）的化合物可用作TRPM8的拮抗剂。这些化合物在治疗许多TRPM8介导的疾病和症状方面具有用处，并可用于制备用于治疗这些疾病和症状的药物和药物组合物。这些疾病的例子包括但不限于偏头痛和神经病性疼痛。式（I）的化合物具有上述结构，其中变量的定义在此提供。
• NOVEL 4-(AZACYCLOALKYL)BENZENE-1,3-DIOL COMPOUNDS AS TYROSINASE INHIBITORS, PROCESS FOR THE PREPARATION THEREOF AND USE THEREOF IN HUMAN MEDICINE AND IN COSMETICS
  申请人：Boiteau Jean-Guy

  公开号：US20110311466A1

  公开（公告）日：2011-12-22

  4-(azacycloalkyl)benzene-1,3-diol compounds are described corresponding to general formula (I) below: Also described, are compositions including the same, processes for preparation thereof and uses thereof in pharmaceutical or cosmetic compositions to treat pigmentary disorders.

  本文描述了符合以下通式（I）的4-(氮杂环烷基)苯-1,3-二酚化合物：同时还描述了包括这些化合物的组合物、制备方法以及在制备药物或化妆品组合物以治疗色素性疾病中的使用。
• 4-(AZACYCLOALKYL)BENZENE-1,3-DIOL COMPOUNDS AS TYROSINASE INHIBITORS, PROCESS FOR THE PREPARATION THEREOF AND USE THEREOF IN HUMAN MEDICINE AND IN COSMETICS
  申请人：BOITEAU Jean-Guy

  公开号：US20130023516A1

  公开（公告）日：2013-01-24

  4-(azacycloalkyl)benzene-1,3-diol compounds are described corresponding to general formula (I) below: Also described, are compositions including the same, processes for preparation thereof and uses thereof in pharmaceutical or cosmetic compositions to treat pigmentary disorders.

  描述了符合下面通式（I）的4-（氮杂环烷基）苯-1,3-二酚化合物：同时还描述了包括这些化合物的组合物、其制备过程以及在制备药物或化妆品组合物中用于治疗色素性疾病的用途。
• TRPM8 ANTAGONISTS AND THEIR USE IN TREATMENTS
  申请人：BROWN James

  公开号：US20130158034A1

  公开（公告）日：2013-06-20

  Compounds of Formula I are useful as antagonists of TRPM8. Such compounds are useful in treating a number of TRPM8 mediated disorders and conditions and may be used to prepare medicaments and pharmaceutical compositions useful for treating such disorders and conditions. Examples of such disorders include, but are not limited to, migraines and neuropathic pain. Compounds of Formula I have the following structure: where the definitions of the variables are provided herein.

  式I的化合物是TRPM8拮抗剂，对于治疗许多TRPM8介导的疾病和症状有用，并可用于制备治疗此类疾病和症状的药物和制剂。此类疾病的例子包括但不限于偏头痛和神经病性疼痛。式I的化合物具有以下结构：其中变量的定义在此提供。