(3-chloro-5-hexyl-2,6-dihydroxyphenyl)(4,5-dichloropyrrol-3-yl)methanone | 491600-94-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-chloro-5-hexyl-2,6-dihydroxyphenyl)(4,5-dichloropyrrol-3-yl)methanone
• 英文别名: (3-Chloro-5-hexyl-2,6-dihydroxyphenyl)(4,5-dichloro-1H-pyrrol-3-yl)methanone；(3-chloro-5-hexyl-2,6-dihydroxyphenyl)-(4,5-dichloro-1H-pyrrol-3-yl)methanone
• CAS: 491600-94-3
• 化学式: C₁₇H₁₈Cl₃NO₃
• 分子量: 390.694
• InChiKey: JCODZTWACRQCLZ-UHFFFAOYSA-N

物化性质

• 溶解度：
  乙醇中≤20mg/ml；DMSO 中≤20mg/ml；二甲基甲酰胺中≤20mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  73.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3-chloro-5-hexyl-2,6-dimethoxyphenyl)(4,5-dichloropyrrol-3-yl)methanone 在 三溴化硼 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 以76%的产率得到(3-chloro-5-hexyl-2,6-dihydroxyphenyl)(4,5-dichloropyrrol-3-yl)methanone
  参考文献：
  名称：

  Revised Structure and Synthesis of Celastramycin A, A Potent Innate Immune Suppressor

  摘要：

  After searching for natural substances that regulate innate immunity using the ex vivo Drosophila culture system, a benzoyl pyrrole-type compound, celastramycin A, was identified and isolated as a potent suppressor. By synthesizing the previously reported structure 1 and another benzoyl pyrrole-type compound 2 reported in a Japanese patent, the correct structure of celastramycin A was confirmed to be 2. Compound 2 suppressed the production of IL-8 (IC50 0.06 mu g/mL) in human umbilical vein endothelial cells (HUVECs).

  DOI：

  10.1021/ol9002306

文献信息

• PROPHYLACTIC OR THERAPEUTIC AGENT FOR PULMONARY HYPERTENSION COMPRISING UNSATURATED 5-MEMBERED HETEROCYCLE-CONTAINING COMPOUND
  申请人：TOHOKU UNIVERSITY

  公开号：US20210299093A1

  公开（公告）日：2021-09-30

  The present invention provides a preventive or therapeutic agent for pulmonary hypertension, including a compound represented by the following formula (I) or a salt thereof: where: -A- represents —NH—, —S—, or —O—; R 1 and R 2 are identical to or different from each other, and each represent a hydrogen atom or an alkyl group; R 3 represents a hydrogen atom, a halogen atom, or an alkyl group; R 4 represents a hydrogen atom or an alkyl group; R 5 represents a hydrogen atom or an alkyl group; R 6 and R 7 are identical to or different each other, and each represent a hydrogen atom, a halogen atom, or an alkyl group; and R 6 and R 7 may form an unsaturated hydrocarbon six-membered ring together with a carbon atom to which R 6 is bonded and a carbon atom to which R 7 is bonded.
• Revised Structure and Synthesis of Celastramycin A, A Potent Innate Immune Suppressor
  作者：Haruhisa Kikuchi、Mizuki Sekiya、Yasuhiro Katou、Kazunori Ueda、Takahiro Kabeya、Shoichiro Kurata、Yoshiteru Oshima

  DOI：10.1021/ol9002306

  日期：2009.4.16

  After searching for natural substances that regulate innate immunity using the ex vivo Drosophila culture system, a benzoyl pyrrole-type compound, celastramycin A, was identified and isolated as a potent suppressor. By synthesizing the previously reported structure 1 and another benzoyl pyrrole-type compound 2 reported in a Japanese patent, the correct structure of celastramycin A was confirmed to be 2. Compound 2 suppressed the production of IL-8 (IC50 0.06 mu g/mL) in human umbilical vein endothelial cells (HUVECs).