3,5-dimethylisoxazole-4-sulfonylhydrazide | 80466-95-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 3,5-dimethylisoxazole-4-sulfonylhydrazide
• 英文别名: 3,5-dimethylisoxazole sulfonyl hydrazide；3,5-Dimethylisoxazole-4-sulfonohydrazide；3,5-dimethyl-1,2-oxazole-4-sulfonohydrazide
• CAS: 80466-95-1
• 化学式: C₅H₉N₃O₃S
• 分子量: 191.211
• InChiKey: HGLLCPZLSLGNBR-UHFFFAOYSA-N

物化性质

• 沸点：
  395.3±52.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-dimethylisoxazole-4-sulfonylhydrazide 生成 4-(3,5-Diphenyl-pyrazole-1-sulfonyl)-3,5-dimethyl-isoxazole
  参考文献：
  名称：

  Cremlyn, Richard J.; Swinbourne, Fred J.; Yung, Kin-Man, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 997 - 1006

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲基异唑 在 氯磺酸 、 hydrazine hydrate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3,5-dimethylisoxazole-4-sulfonylhydrazide
  参考文献：
  名称：

  Development of novel NLRP3-XOD dual inhibitors for the treatment of gout

  摘要：

  Gout is a crystalline-related arthropathy caused by the deposition of monosodium urate (MSU). Acute gouty arthritis is the most common first symptom of gout. Studies have shown that NOD-like receptor protein 3 (NLRP3) inflammasome as pattern recognition receptors can be activated by uric acid crystallization, triggering immune inflammation and causing acute gouty arthritis symptoms. Currently, the treatment of gout mainly includes two basic methods: reducing uric acid and alleviating inflammation. In this paper, 22 novel benzoxazole and benzimidazole derivatives were synthesized from deoxybenzoin oxime derivatives. These compounds have good inhibitory effects on NLRP3 and XOD screened by our research group in the early stage. The inhibitory activities of XOD and NLRP3 and their derivatives were also screened. Notably, compound 9b is a multi-targeting inhibitor of NLRP3 and XOD with excellent potency in treating hyperuricemia and acute gouty arthritis.

  DOI：

  10.1016/j.bmcl.2019.126944

文献信息

• Synthesis of Multi‐substituted Dihydropyrazoles by Copper‐Mediated [4+1] Cycloaddition Reaction of <i>N</i> ‐Sulfonylhydrazones and Sulfoxonium Ylides
  作者：Sipei Hu、Shiying Du、Zuguang Yang、Lingfang Ni、Zhengkai Chen

  DOI：10.1002/adsc.201900212

  日期：2019.7.2

  A general and expeditious approach for the copper mediated synthesis of multi‐functionalized dihydropyrazoles from N‐sulfonylhydrazones and sulfoxonium ylides has been achieved under aerobic oxidative conditions. The formal [4+1] cycloaddition reaction exhibits many notable features and can be easily scaled up to gram scale.

  在好氧氧化条件下，已实现了一种由N-磺酰基hydr和亚砜基铜合成铜介导的多官能化二氢吡唑的通用快速方法。正式的[4 + 1]环加成反应具有许多显着特征，可以轻松按比例放大至克级。
• General Access to <i>N</i> −CF ₃ Secondary Amines and Their Transformation to <i>N</i> −CF ₃ Sulfonamides
  作者：Leibing Wang、Jieping Wang、Sitao Ye、Beihan Jiang、Zihao Guo、Yasir Mumtaz、Wenbin Yi

  DOI：10.1002/anie.202212115

  日期：2022.12.5

  A new and mild method for the generation of HF from triethylsilane and silver fluoride leads to a highly efficient one-pot synthesis of N−CF3 secondary amines. Novel N−CF3 sulfonamides were constructed from these promising amine building blocks and sulfonyl bromides in an unprecedented route.

  一种由三乙基硅烷和氟化银生成 HF 的新型温和方法可实现N -CF 3仲胺的高效一锅法合成。新型N -CF 3磺胺类化合物是通过前所未有的途径由这些有前途的胺结构单元和磺酰溴构建而成的。
• CREMLYN, R. J.;SWINBOURNE, F. J.;YUNG, KIN-MAN, J. HETEROCYCL. CHEM., 1981, 18, N 5, 997-1006
  作者：CREMLYN, R. J.、SWINBOURNE, F. J.、YUNG, KIN-MAN

  DOI：——

  日期：——
• Development of novel NLRP3-XOD dual inhibitors for the treatment of gout
  作者：Weiwei Wang、Jing Pang、Eun Hee Ha、Mengze Zhou、Zhubin Li、Sheng Tian、Huanqiu Li、Qinghua Hu

  DOI：10.1016/j.bmcl.2019.126944

  日期：2020.2

  Gout is a crystalline-related arthropathy caused by the deposition of monosodium urate (MSU). Acute gouty arthritis is the most common first symptom of gout. Studies have shown that NOD-like receptor protein 3 (NLRP3) inflammasome as pattern recognition receptors can be activated by uric acid crystallization, triggering immune inflammation and causing acute gouty arthritis symptoms. Currently, the treatment of gout mainly includes two basic methods: reducing uric acid and alleviating inflammation. In this paper, 22 novel benzoxazole and benzimidazole derivatives were synthesized from deoxybenzoin oxime derivatives. These compounds have good inhibitory effects on NLRP3 and XOD screened by our research group in the early stage. The inhibitory activities of XOD and NLRP3 and their derivatives were also screened. Notably, compound 9b is a multi-targeting inhibitor of NLRP3 and XOD with excellent potency in treating hyperuricemia and acute gouty arthritis.
• Cremlyn, Richard J.; Swinbourne, Fred J.; Yung, Kin-Man, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 997 - 1006
  作者：Cremlyn, Richard J.、Swinbourne, Fred J.、Yung, Kin-Man

  DOI：——

  日期：——