8-bromodibenzo[b,d]furan-3-sulfonyl chloride | 1025719-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 8-bromodibenzo[b,d]furan-3-sulfonyl chloride
• 英文别名: 8-Bromo-3-dibenzofuransulfonyl chloride；8-bromodibenzofuran-3-sulfonyl chloride
• CAS: 1025719-43-0
• 化学式: C₁₂H₆BrClO₃S
• 分子量: 345.601
• InChiKey: DEVGIDWQMQZRDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-bromodibenzo[b,d]furan-3-sulfonyl chloride 在 四(三苯基膦)钯 、 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (S)-methyl 2-(8-cyanodibenzo[b,d]furan-3-sulfonamido)-3-methylbutanoate
  参考文献：
  名称：

  Discovery of potent and selective matrix metalloprotease 12 inhibitors for the potential treatment of chronic obstructive pulmonary disease (COPD)

  摘要：

  Chronic obstructive pulmonary disease (COPD) is an inflammatory lung disease associated with irreversible progressive airflow limitation. Matrix metalloproteinase-12 (MMP-12) has been characterized to be one of the major proteolytic enzymes to induce airway remodeling, destruction of elastin and the aberrant remodeling of damaged alveoli in COPD and asthma. The goal of this project is to develop and identify an orally potent and selective small molecule inhibitor of MMP-12 for treatment of COPD and asthma. Syntheses and structure-activity relationship (SAR) studies of a series of dibenzofuran (DBF) sulfonamides as MMP-12 inhibitors are described. Potent inhibitors of MMP-12 with excellent selectivity against other MMPs were identified. Compound 26 (MMP118), which exhibits excellent oral efficacy in the MMP-12 induced ear-swelling inflammation and lung inflammation mouse models, had been successfully advanced into Development Track status. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.046
• 作为产物：
  描述：

  3-氨基二苯并呋喃 在 盐酸 、 二氧化硫 、 溴 、 氯 、 溶剂黄146 、 copper dichloride 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 34.0h， 生成 8-bromodibenzo[b,d]furan-3-sulfonyl chloride
  参考文献：
  名称：

  Discovery of potent and selective matrix metalloprotease 12 inhibitors for the potential treatment of chronic obstructive pulmonary disease (COPD)

  摘要：

  Chronic obstructive pulmonary disease (COPD) is an inflammatory lung disease associated with irreversible progressive airflow limitation. Matrix metalloproteinase-12 (MMP-12) has been characterized to be one of the major proteolytic enzymes to induce airway remodeling, destruction of elastin and the aberrant remodeling of damaged alveoli in COPD and asthma. The goal of this project is to develop and identify an orally potent and selective small molecule inhibitor of MMP-12 for treatment of COPD and asthma. Syntheses and structure-activity relationship (SAR) studies of a series of dibenzofuran (DBF) sulfonamides as MMP-12 inhibitors are described. Potent inhibitors of MMP-12 with excellent selectivity against other MMPs were identified. Compound 26 (MMP118), which exhibits excellent oral efficacy in the MMP-12 induced ear-swelling inflammation and lung inflammation mouse models, had been successfully advanced into Development Track status. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.046

文献信息

• TRICYCLIC COMPOUNDS AS MATRIX METALLOPROTEINASE INHIBITORS
  申请人：LI Wei

  公开号：US20100227859A1

  公开（公告）日：2010-09-09

  The present teachings relate to compounds of formula I: and pharmaceutically acceptable salts and esters thereof, wherein R1, R2, R3, R4, X, and Y are as defined herein. The present teachings also provide methods of making the compounds of formula I and methods of inhibiting matrix metalloproteinases, in particular, MMP-12, that may be involved in pathological disorders found in mammals, including a human.

  目前的教导与式I的化合物有关：及其药用盐和酯，其中R1、R2、R3、R4、X和Y如本文所定义。目前的教导还提供了制备式I化合物的方法以及抑制基质金属蛋白酶的方法，特别是可能参与哺乳动物中发现的病理性疾病，包括人类。
• [EN] DIBENZOFURAN DERIVATIVE CATHEPSIN K INHIBITOR, PREPARATION METHOD THEREFOR AND MEDICAL USE THEREOF<br/>[FR] INHIBITEUR DE LA CATHEPSINE K DÉRIVÉ DU DIBENZOFURANE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION MÉDICALE<br/>[ZH] 一种二苯并呋喃类衍生物组织蛋白酶K抑制剂及其制备方法和医药用途
  申请人：SHENZHEN SALUBRIS PHARM CO LTD

  公开号：WO2021147882A1

  公开（公告）日：2021-07-29

  提供了一系列的组织蛋白酶K的抑制剂，尤其提供了一种二苯并呋喃衍生物组织蛋白酶K的抑制剂，属于化学药物技术领域。还涉及包含这些化合物的药物组合物以及使用该化合物治疗骨关节炎等疾病的药物中的用途。
• WO2008/57254
  申请人：——

  公开号：——

  公开（公告）日：——
• A Selective Matrix Metalloprotease 12 Inhibitor for Potential Treatment of Chronic Obstructive Pulmonary Disease (COPD): Discovery of (<i>S</i>)-2-(8-(Methoxycarbonylamino)dibenzo[<i>b</i>,<i>d</i>]furan-3-sulfonamido)-3-methylbutanoic acid (MMP408)
  作者：Wei Li、Jianchang Li、Yuchuan Wu、Junjun Wu、Rajeev Hotchandani、Kristina Cunningham、Iain McFadyen、Joel Bard、Paul Morgan、Franklin Schlerman、Xin Xu、Steve Tam、Samuel J. Goldman、Cara Williams、Joseph Sypek、Tarek S. Mansour

  DOI：10.1021/jm900093d

  日期：2009.4.9

  Matrix metalloprotease 12 plays a significant role in airway inflammation and remodeling. Increased expression and production of MMP-12 have-been found in the lung of human COPD patients. MMP408 (14), a potent and selective MMP-12 inhibitor, was derived from a potent matrix metalloprotease 2 and 13 inhibitor via lead optimization and has good physical properties and bioavailability. The compound blocks rhMMP-12-induced lung inflammation in a mouse model and was advanced for further development for the treatment of COPD.
• [EN] TRICYCLIC COMPOUNDS AS MATRIX METALLOPROTEINASE INHIBITORS<br/>[FR] COMPOSÉS TRICYCLIQUES SERVANT D'INHIBITEURS DES MÉTALLOPROTÉASES MATRICIELLES
  申请人：WYETH CORP

  公开号：WO2008057254A2

  公开（公告）日：2008-05-15

  [EN] The present invention relates to compositions of the formula (I): and pharmaceutically acceptable salts, hydrates, or esters thereof, wherein R¹, R², R³, R⁴, R⁵, X, and Y are as defined herein. The present teachings also provide methods of making the compounds of formula I, and methods of treating pathologic conditions or disorders mediated wholly or in part by matrix metalloproteinases, such as asthma and chronic obstructive pulmonary disease, comprising administering a therapeutically effective amount of a compound of formula (I) to a mammal (e.g., a human) in need thereof.
  [FR] La présente invention concerne des composés de formule (I) : et des sels, hydrates ou esters acceptables du point de vue pharmaceutique de ceux-ci, R¹, R², R³, R⁴, R⁵, X et Y étant tels que définis ici. La présente invention concerne également des procédés de fabrication des composés de formule (I) et des procédés de traitement d'affections ou troubles pathologiques induits entièrement ou en partie par des métalloprotéases matricielles, tels que l'asthme et une bronchopneumopathie chronique obstructive, lesquels consistent à administrer une quantité efficace du point de vue thérapeutique d'un composé de formule (I) à un mammifère (par exemple à un humain) qui en a besoin.