5-Methanesulfonamido-6-(2,-thienylthio)-1-indanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-Methanesulfonamido-6-(2,-thienylthio)-1-indanone
• 英文别名: N-[1-Oxo-6-(thiophen-2-ylsulfanyl)-indan-5-yl]-methanesulfonamide；N-(1-oxo-6-thiophen-2-ylsulfanyl-2,3-dihydroinden-5-yl)methanesulfonamide
• 化学式: C₁₄H₁₃NO₃S₃
• 分子量: 339.46
• InChiKey: MNEGJUFMXCJITI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氨基茚旦 在 吡啶 、 chromium(VI) oxide 、 盐酸 、 氢氧化钾 、 sodium hydroxide 、 tetrafluoroboric acid 、 三氟甲磺酸三甲基硅酯 、 溴 、 铁粉 、 铜 、 氯化铵 、 溶剂黄146 、 三乙胺 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 5-Methanesulfonamido-6-(2,-thienylthio)-1-indanone
  参考文献：
  名称：

  Cyclooxygenase-2 Inhibitors. Synthesis and Pharmacological Activities of 5-Methanesulfonamido-1-indanone Derivatives

  摘要：

  The recent discovery of an alternative form cyclooxygenase (cyclooxygenase-2, COX-2), which has been proposed to play a significant role in inflammatory conditions, may provide an opportunity to develop anti-inflammatory drugs with fewer side effects than existing nonsteroidal anti-inflammatory drugs (NSAIDs). We have now identified 6-[(2,4-difluorophenyl)thio]-5-methanesulfonamido-1-indanone (20) (L-745,337) as a potent, selective, and orally active COX-2 inhibitor. The structure-activity relationships in this series have been extensively studied. Ortho- and para-substituted B-phenyl substitutents are optimal for in vitro potency. Replacement of this phenyl ring by a variety of heterocycles gave compounds that were less active. The methanesulfonamido group seems to be the optimal group at the 5-position of the indanone system. Compound 20 has an efficacy profile that is superior or comparable to that of the nonselective COX inhibitor indomethacin in animal models of inflammation, pain, and fever and appears to be nonulcerogenic within the dosage ranges required for functional efficacy. Although 20 and its oxygen linkage analog 2 (flosulide) are equipotent in the in vitro assays, compound 20 is more potent in the rat paw edema assay, has a longer t(1/2) in squirrel monkeys, and seems less ulcergenic than 2 in rats.

  DOI：

  10.1021/jm00025a007

文献信息

• Alkanesulfonamido-1-indanone derivatives as inhibitors of cyclooxygenase
  申请人：Merck Frosst Canada, Inc.

  公开号：US05409944A1

  公开（公告）日：1995-04-25

  Disclosed are compounds of Formula I useful in the treatment of cyclooxygenase mediated diseases such as pain, fever and inflammation of a variety of conditions including rheumatic fever, symptoms associated with influenza or other viral infections, common cold, low back and neck pain, dysmenorrhea, headache, toothache, sprains and strains, myositis, neuralgia, synovitis, arthritis, including rheumatoid arthritis degenerative joint diseases (osteoarthritis), gout and ankylosing spondylitis, bursitis, burns, injuries. ##STR1##

  揭示了Formula I的化合物，可用于治疗环氧合酶介导的疾病，如疼痛、发热和炎症，包括风湿热、与流感或其他病毒感染相关的症状、普通感冒、腰背痛、颈部疼痛、月经痛、头痛、牙痛、扭伤和拉伤、肌炎、神经痛、滑囊炎、关节炎，包括风湿性关节炎、退行性关节疾病（骨关节炎）、痛风和强直性脊柱炎、滑囊炎、烧伤、受伤。
• Pharmaceutical formulation containing muscle relaxant and COX-II inhibitor
  申请人：Sen Nilendu

  公开号：US20050100594A1

  公开（公告）日：2005-05-12

  Disclosed is an extended release pharmaceutical formulation comprising a muscle relaxant drug, such as tizanidine, in combination with a cyclooxygenase-2 inhibitor, such as valdecoxib. The formulations are useful in the treatment and management of painful inflammatory conditions associated with, for example, skeletal muscle spasms.

  本发明公开了一种缓释药物制剂，该制剂由肌肉松弛剂药物（如替扎尼丁）与环氧化酶-2 抑制剂（如伐地昔布）组合而成。该制剂可用于治疗和控制与骨骼肌痉挛等相关的疼痛性炎症。
• Topical pharmaceutical compositions
  申请人：Krishnan Anandi

  公开号：US20050096371A1

  公开（公告）日：2005-05-05

  A hydroalcoholic topical pharmaceutical composition is provided comprising a therapeutically effective amount of a therapeutic agent comprising one or more selective cyclooxygenase-2 (COX-2) inhibitors or pharmaceutically acceptable salts or esters thereof solubilized in a solubilizing amount of a penetration vehicle system comprising a skin penetration enhancing effective amount of at least one monohydric alcohol and at least two non-volatile organic compounds selected from the group consisting of pyrrolidones, polyol ethers, polyols and mixtures thereof. Also provided is a process for its preparation.

  本发明提供了一种水醇局部药物组合物，该组合物包含治疗有效量的治疗剂，该治疗剂包含一种或多种选择性环氧化酶-2 (COX-2) 抑制剂或其药学上可接受的盐或酯，该治疗剂溶解在渗透载体系统的溶解量中，该渗透载体系统包含皮肤渗透增强有效量的至少一种一元醇和至少两种非挥发性有机化合物，这些非挥发性有机化合物选自由吡咯烷酮、多元醇醚、多元醇及其混合物组成的组。此外，还提供了一种制备方法。
• COX-2 INHIBITORS IN COMBINATION WITH NMDA-BLOCKERS FOR TREATING PAIN
  申请人：Algos Pharmaceutical Corporation

  公开号：EP1146905A1

  公开（公告）日：2001-10-24
• US5409944A
  申请人：——

  公开号：US5409944A

  公开（公告）日：1995-04-25