2,4-二氯-3-甲基苯磺酰氯 | 69145-58-0

• 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: 2,4-二氯-3-甲基苯磺酰氯
• 英文名称: 2,4-dichloro-3-methylbenzenesulfonyl chloride
• CAS: 69145-58-0
• 化学式: C₇H₅Cl₃O₂S
• 分子量: 259.541
• InChiKey: XMKNKDQXFBQJDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  1
• 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

安全信息

• 海关编码：
  2904909090

反应信息

• 作为反应物：
  描述：

  2,4-二氯-3-甲基苯磺酰氯 在 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 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：

  2,6-二氯甲苯 在 氯磺酸 作用下， 反应 4.0h， 以85%的产率得到2,4-二氯-3-甲基苯磺酰氯
  参考文献：
  名称：

  [EN] NON-PEPTIDE BRADYKININ ANTAGONISTS AND PHARMACEUTICAL COMPOSITIONS THEREFROM
  [FR] ANTAGONISTES DE BRADYKININE NON-PEPTIDIQUES ET COMPOSITIONS PHARMACEUTIQUES CONSTITUEES DE CES COMPOSES

  摘要：

  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。

  公开号：

  WO2006040004A1

文献信息

• Novel n(phenylsulphonyl)glycine derivatives and their therapeutic use
  申请人：——

  公开号：US20040063725A1

  公开（公告）日：2004-04-01

  The present invention relates to novel N-(phenylsulphonyl)glycyl-glycine compounds, which are defined by formula I and the description, as well as their method of preparation and their use in therapeutics 1

  本发明涉及一种新颖的N-(苯磺酰基)甘氨酰甘氨酸化合物，其由式I和描述所定义，以及它们的制备方法及在治疗中的用途。
• From Bradykinin B2 Receptor Antagonists to Orally Active and Selective Bradykinin B1 Receptor Antagonists
  作者：Martine Barth、Michel Bondoux、Jean-Michel Luccarini、Vincent Peyrou、Pierre Dodey、Didier Pruneau、Christine Massardier、Jean-Luc Paquet

  DOI：10.1021/jm2016057

  日期：2012.3.22

  The bradykinin (BK) B1 receptor is an attractive target for the treatment of chronic pain and inflammation. Starting from a dual B1 and B2 antagonist, novel antagonists were designed that display low-nanomolar affinity for human B1 receptor and selectivity over B2. Initially, potent imidazoline derivatives were studied, but these compounds suffered from low bioavailability. This issue could be overcome

  缓激肽（BK）B1受体是治疗慢性疼痛和炎症的诱人靶标。从双重B1和B2拮抗剂开始，设计了新型拮抗剂，这些拮抗剂显示出对人B1受体的低纳摩尔亲和力和对B2的选择性。最初，研究了有效的咪唑啉衍生物，但这些化合物的生物利用度较低。该问题可以通过使用碱性较低的氨基衍生物来产生口服活性化合物来克服。
• Novel arylsulphonamide derivatives and use thereof as therapeutic agents
  申请人：Barth Martine

  公开号：US20060084699A1

  公开（公告）日：2006-04-20

  The present invention relates to novel arylsulphonamide compounds, defined by formula I and the description, as well as their method of preparation and their therapeutic use.

  本发明涉及一种新型芳基磺酰胺化合物，其由式I和描述定义，以及它们的制备方法和治疗用途。
• Benzenesulphonamide derivatives, method for production and use thereof for treatment of pain
  申请人：Barth Martine

  公开号：US20060178360A1

  公开（公告）日：2006-08-10

  The present invention concerns novel benzenesulphonamide compounds, defined by formula I and the description, their method of preparation and their use in therapy.

  本发明涉及新型苯磺酰胺化合物，由公式I和描述所定义，其制备方法及在治疗中的用途。
• Tetraphenylphosphonium bromide-catalyzed ‘Halex’ fluorination of chloroaryl sulfonyl chlorides
  作者：Hiroshi Suzuki、Hiroyuki Kageyama、Yasuo Yoshida、Yoshikazu Kimura

  DOI：10.1016/s0022-1139(00)82362-3

  日期：1991.12

  Halogen-exchange of chloroaryl sulfonylchloride derivatives with spray-dried potassium fluoride was found to proceed efficiently by employing tetraphenylphosphonium bromide as a catalyst. Subsequent desulfonylation of the fluoroaryl sulfonyl derivatives readily afforded fluoroaromatics under acidic condition.

  通过使用溴化四苯基phenyl作为催化剂，发现氯芳基磺酰氯衍生物与喷雾干燥的氟化钾的卤素交换有效地进行。氟芳基磺酰基衍生物的随后的磺酰化在酸性条件下容易得到氟代芳族化合物。