5-nitro-6-bromo-1-indanone ethylene ketal | 158205-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-nitro-6-bromo-1-indanone ethylene ketal
• 英文别名: 6-bromo-5-nitro-1-indanone ethylene ketal；5-Nitro-6-bromo-1-indanone ethylene acetal；5-bromo-6-nitrospiro[1,2-dihydroindene-3,2'-1,3-dioxolane]
• CAS: 158205-21-1
• 化学式: C₁₁H₁₀BrNO₄
• 分子量: 300.109
• InChiKey: WEFOWVHTRHKHAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitro-6-bromo-1-indanone ethylene ketal 在 盐酸 、 氢氧化钾 、 potassium carbonate 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 44.0h， 生成 甲磺酰胺,N-[6-[(2,4-二氟苯基)硫代]-2,3-二氢-1-羰基-1H-茚-5-基]-
  参考文献：
  名称：

  Synthesis of 5-Methanesulfonamido-6-(2,4-Difluorophenylthio)-1-Indanone

  摘要：

  The ethylene ketal of 5-nitro-6-bromo-1-indanone 6 was prepared via oxidation of N-(6-Bromo-5-indanyl)-acetamide 1. A subsequent mild displace; merit and elaboration to 6-thiosubstituted-5amino indanone derivative 10 is also described.

  DOI：

  10.1080/00397919508011826
• 作为产物：
  描述：

  N-(6-溴-2,3-二氢-1H-茚-5-基)乙酰胺 在 chromium(VI) oxide 、 盐酸 、 tetrafluoroboric acid 、 三氟甲磺酸三甲基硅酯 、 铜 、 溶剂黄146 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 5-nitro-6-bromo-1-indanone ethylene ketal
  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

• 5-methanesulfonamido-1-indanones as an inhibitor of cyclooxygenase-2
  申请人：Merck Frosst Canada Inc.

  公开号：US05604260A1

  公开（公告）日：1997-02-18

  The Compound of Formula I and pharmaceutically acceptable salts thereof in the treatment of cyclooxygenase-2 mediated diseases are disclosed.

  公式I的化合物及其药用盐在治疗环氧合酶-2介导的疾病中被披露。
• 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。
• USRE038103E1
  申请人：——

  公开号：——

  公开（公告）日：——
• US5409944A
  申请人：——

  公开号：US5409944A

  公开（公告）日：1995-04-25
• Synthesis of 5-Methanesulfonamido-6-(2,4-Difluorophenylthio)-1-Indanone
  作者：John Scheigetz、Robert Zamboni、Bruno Roy

  DOI：10.1080/00397919508011826

  日期：1995.9

  The ethylene ketal of 5-nitro-6-bromo-1-indanone 6 was prepared via oxidation of N-(6-Bromo-5-indanyl)-acetamide 1. A subsequent mild displace; merit and elaboration to 6-thiosubstituted-5amino indanone derivative 10 is also described.