4-(2-Phenylethynyl)benzenesulfonyl chloride | 203639-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-Phenylethynyl)benzenesulfonyl chloride
• CAS: 203639-82-1
• 化学式: C₁₄H₉ClO₂S
• 分子量: 276.743
• InChiKey: JBVXOSUDJJOHKG-UHFFFAOYSA-N

物化性质

• 沸点：
  410.0±28.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-(2-Phenylethynyl)benzenesulfonyl chloride 在 氢氧化钾 、 三乙胺 作用下， 生成 (Z)-7-[(1S,2R,3R,4R)-3-(4-Phenylethynyl-benzenesulfonylamino)-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid
  参考文献：
  名称：

  双环[2.2.1]庚烷和6,6-二甲基双环[3.1.1]庚烷衍生物：口服活性，有效和选择性的前列腺素D2受体拮抗剂。

  摘要：

  DOI：

  10.1021/jm970343g
• 作为产物：
  描述：

  1-溴-4-(苯基乙炔基)苯 在 正丁基锂 、 磺酰氯 、 二氧化硫 作用下， 生成 4-(2-Phenylethynyl)benzenesulfonyl chloride
  参考文献：
  名称：

  Highly Selective and Orally Active Inhibitors of Type IV Collagenase (MMP-9 and MMP-2):  N-Sulfonylamino Acid Derivatives

  摘要：

  Various N-sulfonylamino acid derivatives were synthesized and evaluated for their in vitro and in vivo activities to inhibit type IV collagenase (MMP-9 and MMP-2). When the amino acid residue and the sulfonamide moiety were modified, their inhibitory activities were greatly affected by the structure of the sulfonamide moiety. A series of aryl sulfonamide derivatives containing biaryl, tetrazole, amide, and triple bond were found to be potent and highly selective inhibitors of MMP-9 and MMP-2 In addition, these compounds were orally active in animal models of tumor growth and metastasis. These results revealed the potential of the N-sulfonylamino acid derivatives as a new type of candidate drug for the treatment of cancer.

  DOI：

  10.1021/jm9707582

文献信息

• The discovery and structure—activity relationships of nonpeptide, low molecular weight antagonists selective for the endothelin ETB receptor
  作者：Ming Fai Chan、Adam Kois、Erik J. Verner、Bore G. Raju、Rosario S. Castillo、Chengde Wu、Ilya Okun、Fiona D. Stavros、V.N. Balaji

  DOI：10.1016/s0968-0896(98)80010-2

  日期：1998.12

  The systematic modification of the ETA selective N-(5-isoxazolyl)benzene-sulfonamide endothelin antagonists to give ETB selective antagonists is reported. The reversal in selectivity was brought about by substitution of the 4-position with aryl and substituted aryl groups. Of all the aromatic substituents studied, the para-tolyl group gave rise to the most active and selective ETB antagonist. Larger substituents caused a decrease in both ETB activity and selectivity. A similar trend was observed by substitution at the 5-position of the N-(5-isoxazolyl)-2-thiophenesulfonamide ETA receptor antagonists. The para-tolyl group was again found to be optimal for the ETB activity and selectivity. The structural features that were found to be favorable for binding to the ETB receptor, that is, the presence of a linear, conjugated pi-system of definite shape and size, have been successfully incorporated into the design of ETB selective polycyclic aromatic sulfonamides antagonists. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Highly Selective and Orally Active Inhibitors of Type IV Collagenase (MMP-9 and MMP-2):  <i>N</i>-Sulfonylamino Acid Derivatives
  作者：Yoshinori Tamura、Fumihiko Watanabe、Takuji Nakatani、Ken Yasui、Masahiro Fuji、Tadafumi Komurasaki、Hiroshige Tsuzuki、Ryuji Maekawa、Takayuki Yoshioka、Kenji Kawada、Kenji Sugita、Mitsuaki Ohtani

  DOI：10.1021/jm9707582

  日期：1998.2.1

  Various N-sulfonylamino acid derivatives were synthesized and evaluated for their in vitro and in vivo activities to inhibit type IV collagenase (MMP-9 and MMP-2). When the amino acid residue and the sulfonamide moiety were modified, their inhibitory activities were greatly affected by the structure of the sulfonamide moiety. A series of aryl sulfonamide derivatives containing biaryl, tetrazole, amide, and triple bond were found to be potent and highly selective inhibitors of MMP-9 and MMP-2 In addition, these compounds were orally active in animal models of tumor growth and metastasis. These results revealed the potential of the N-sulfonylamino acid derivatives as a new type of candidate drug for the treatment of cancer.
• Bicyclo[2.2.1]heptane and 6,6-Dimethylbicyclo[3.1.1]heptane Derivatives:  Orally Active, Potent, and Selective Prostaglandin D₂ Receptor Antagonists
  作者：Tatsuo Tsuri、Tsunetoshi Honma、Yoshiharu Hiramatsu、Toshihiko Okada、Hiroshi Hashizume、Susumu Mitsumori、Masanao Inagaki、Akinori Arimura、Kiyoshi Yasui、Fujio Asanuma、Junji Kishino、Mitsuaki Ohtani

  DOI：10.1021/jm970343g

  日期：1997.10.1