3-(溴甲基)-2,4-二氯苯-1-磺酰氯 | 188440-21-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(溴甲基)-2,4-二氯苯-1-磺酰氯
• 英文名称: 3-bromomethyl-2,4-dichlorobenzenesulphonyl chloride
• 英文别名: 2,4-dichloro-3-bromomethyl-benzensulfonyl chloride；2,4-dichloro-3-bromomethylbenzenesulfonyl chloride；3-bromomethyl-2,4-dichlorobenzenesulfonyl chloride；3-(Bromomethyl)-2,4-dichlorobenzene-1-sulfonyl chloride；3-(bromomethyl)-2,4-dichlorobenzenesulfonyl chloride
• CAS: 188440-21-3
• 化学式: C₇H₄BrCl₃O₂S
• 分子量: 338.437
• InChiKey: ZGYRSDUHWLVCRB-UHFFFAOYSA-N

物化性质

• 沸点：
  385.8±42.0 °C(Predicted)
• 密度：
  1.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(溴甲基)-2,4-二氯苯-1-磺酰氯 在 lithium hydroxide 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 1-[2,4-dichloro-3-(2,4-dimethyl-quinolin-8-yloxymethyl)-benzenesulfonylamino]-cyclopentanecarboxylic acid
  参考文献：
  名称：

  Design and Synthesis of Novel Sulfonamide-Containing Bradykinin hB₂ Receptor Antagonists. 2. Synthesis and Structure−Activity Relationships of α,α-Cycloalkylglycine Sulfonamides

  摘要：

  Recently we reported on the design and synthesis of a novel class of selective nonpeptide bradykinin (BK) B-2 receptor antagonists (J. Med. Chem. 2006, 3602-3613). This work led to the discovery of MEN 15442, an antagonist with subnanomolar affinity for the human B2 receptor (hB2R), which also displayed significant and prolonged activity in vivo (for up to 210 min) against BK-induced bronchoconstriction in the guinea-pig at a dose of 300 nmol/kg (it), while demonstrating only a slight effect on BK-induced hypotension. Here we describe the further optimization of this series of compounds aimed at maximizing the effect on bronchoconstriction and minimizing the effect on hypotension, with a view to developing topically delivered drugs for airway diseases. The work led to the discovery of MEN 16132, a compound which, after intratracheal or aerosol administration, inhibited, in a dose-dependent manner, BK-induced bronchoconstricton in the airways, while showing minimal systemic activity. This compound was selected as a preclinical candidate for the topical treatment of airway diseases involving kinin B2 receptor stimulation.

  DOI：

  10.1021/jm061143k
• 作为产物：
  描述：

  2,4-二氯-3-甲基苯磺酰氯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 以47%的产率得到3-(溴甲基)-2,4-二氯苯-1-磺酰氯
  参考文献：
  名称：

  发现新的喹啉磺酰胺衍生物作为有效，选择性和口服活性的RORγ反向激动剂。

  摘要：

  使用Gal4 /RORγ-LBD荧光素酶报告基因基因分析方法对Inventiva化合物库进行的高通量筛选导致发现了一系列新的喹啉磺酰胺类药物作为RORγ抑制剂，最终产生了口服后具有有趣体内特征的先导化合物行政。在小鼠的目标参与模型中评估了该铅，该模型在免疫激发后降低了IL-17细胞因子的产生。它也被证明在多发性硬化症模型（EAE）中有效，从而降低了疾病评分。本文描述了这些衍生物的合成，结构活性关系（SAR）和生物学活性。

  DOI：

  10.1016/j.bmcl.2019.05.015

文献信息

• Heterocyclic benzenesulphonamide compounds as bradykinine antagonists
  申请人：Fournier Industrie et Sante

  公开号：US06479515B1

  公开（公告）日：2002-11-12

  The invention concerns compounds selected among the group consisting of (i) compounds of formula (I) wherein: Het1 represents a nitrogenous heterocycle with 5 apices, in particular imidazole, pyrazole, or triazole; Het2 represents a nitrogenous heterocycle with 4, 5 or 6 apices, selected among the heterocycles: (II) wherein R1 and R2 are defined as mentioned in the description; and (ii) their additive salts. The invention also concerns the method for preparing said compounds and their use in therapy, in particular for treating pathologies involving bradykinine.

  这项发明涉及选自以下组合的化合物：(i) 公式(I)中的化合物，其中：Het1代表具有5个顶点的氮杂环，特别是咪唑、吡唑或三唑；Het2代表具有4、5或6个顶点的氮杂环，选自以下杂环：(II)，其中R1和R2如描述中所述定义；以及(ii) 它们的加合盐。该发明还涉及制备所述化合物的方法以及它们在治疗中的用途，特别是用于治疗涉及激肽酶的病理问题。
• [EN] NON-PEPTIDE BRADYKININ ANTAGONISTS AND PHARMACEUTICAL COMPOSITIONS THEREFROM<br/>[FR] ANTAGONISTES DE BRADYKININE NON-PEPTIDIQUES ET COMPOSITIONS PHARMACEUTIQUES CONSTITUEES DE CES COMPOSES
  申请人：LUSO FARMACO INST

  公开号：WO2006040004A1

  公开（公告）日：2006-04-20

  Non-peptide compounds having activity as selective antagonists of bradykinin (BK) B2 receptor. The compounds are chemically characterized by the presence of an amino acid alpha substituted with a cyclic group and by a tetraalkylammonium group.

  具有作为布雷金肽（BK）B2受体选择性拮抗剂活性的非肽化合物。这些化合物在化学上的特征是存在一个带有环状基团的α-氨基酸取代基和一个四烷基铵基团。
• [EN] BASIC NON-PEPTIDE BRADYKININ ANTAGONISTS AND PHARMACEUTICAL COMPOSITIONS THEREFROM<br/>[FR] ANTAGONISTES DE BRADYKININE NON PEPTIDIQUE DE BASE ET COMPOSITIONS PHARMACEUTIQUES A BASE DESDITS ANTAGONISTES
  申请人：MENARINI RICERCHE SPA

  公开号：WO2003103671A1

  公开（公告）日：2003-12-18

  Non-peptide compounds of formula (I) having activity as specific antagonists of bradykinin (BK) B2 receptor. The compounds are chemically characterized by the presence of an alpha, alpha-disubstituted amino acid at least one amino group, free or salified, or the corresponding ammonium quaternary salt. These BK receptor antagonists are a novel class of medicaments which can be used in all the disorders in which said receptors are involved.

  化学式为(I)的非肽类化合物具有作为布雷金肽(BK) B2受体特异性拮抗剂的活性。这些化合物在化学上的特征是至少有一个氨基团存在α，α-二取代氨基酸，自由或盐化，或相应的铵季铵盐。这些BK受体拮抗剂是一类新型药物，可用于所有涉及该受体的疾病中。
• Non-peptide bradykinin antagonists and pharmaceutical compositions therefrom
  申请人：Felicetti Patrizia

  公开号：US20070281944A1

  公开（公告）日：2007-12-06

  Disclosed are non-peptide compounds having activity as selective antagonists of bradykinin (BK) B2 receptor. The compounds are chemically characterized by the presence of an amino acid alpha substituted with a cyclic group and by a tetraalkylammonium group. Also disclosed are pharmaceutical compositions containing the compound, and methods of using the compounds to treat patients having conditions, disorders or diseases involving activation of bradykinin B2 receptor.

  本发明涉及一种具有选择性拮抗激活剂作用的非肽类化合物，其与布雷地酮（BK）B2受体相互作用。该化合物化学特征在于存在带有环状基团的氨基酸α取代物和四烷基铵基团。此外，还揭示了含有该化合物的制药组合物，并且揭示了使用该化合物治疗患有与布雷地酮B2受体激活有关的疾病、疾病或病情的患者的方法。
• 1-Benzenesulfonyl pyrrolidine derivatives as bradykinin receptor antagonists
  申请人：Fournier Industrie et Sante

  公开号：US06211181B1

  公开（公告）日：2001-04-03

  This invention relates to compounds of the formula where X is halogen, R1 is H or a C1-C3 alkyl, R2 is H or OH and R3 is one of in which A is a single bond or a —CO(CH2)p—NH— group, R4 is H or —C(═NR5)NHR′5, R5 and R′5 are each H or a C1-C6 alkyl group, R6 is H or a C1-C3 alkyl group, m is 0, 1 or 2; n is 2, 3 or 4; p is 1, 2 or 3; plus their acid addition salts. The invention likewise relates to the method for their preparation and their therapeutic applications.

  本发明涉及以下公式的化合物，其中X是卤素，R1是H或C1-C3烷基，R2是H或OH，R3是其中之一，其中A是单键或—CO(CH2)p—NH—基团，R4是H或—C(═NR5)NHR′5，R5和R′5分别是H或C1-C6烷基，R6是H或C1-C3烷基，m为0、1或2；n为2、3或4；p为1、2或3；以及它们的酸加成盐。本发明还涉及它们的制备方法和治疗应用。