3-methyl-4-nitro-1-phenyl-1H-pyrazole | 90946-24-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-4-nitro-1-phenyl-1H-pyrazole
• 英文别名: 3-methyl-4-nitro-1-phenylpyrazole；3-methyl-4-nitro-1-phenyl-1H-pyrazole；3-Methyl-4-nitro-1-phenyl-1H-pyrazol；3-Methyl-4-nitro-1-phenyl-pyrazol；3-Methyl-4-nitro-1-phenylpyrazol
• CAS: 90946-24-0
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: VVIWGTQYOWMDGV-UHFFFAOYSA-N

物化性质

• 熔点：
  109.5-110 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  337.8±22.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-4-nitro-1-phenyl-1H-pyrazole 在 palladium on activated charcoal 、 乙醇 、 一水合肼 作用下， 生成 N-(3-methyl-1-phenyl-1H-pyrazol-4-yl)amine
  参考文献：
  名称：

  667.与氨基吡唑的skraup反应

  摘要：

  DOI：

  10.1039/jr9580003259
• 作为产物：
  描述：

  3-甲基-1-苯基吡唑 在 硝酸 、 乙酸酐 作用下， 生成 3-methyl-4-nitro-1-phenyl-1H-pyrazole
  参考文献：
  名称：

  Dal Monte; Casoni, Gazzetta Chimica Italiana, 1959, vol. 89, p. 1539,1541

  摘要：

  DOI：

文献信息

• Reactions of pyrazoles and pyrazolium salts with complex metal hydrides and organometallic reagents. Synthesis of pyrazolines and pyrazolidines
  作者：Purificación Cuadrado、Ana M. González-Nogal、Senén Martínez

  DOI：10.1016/s0040-4020(97)00514-0

  日期：1997.6

  2-Pyrazolin-4-oximes have been synthesized by reaction of 4-nitroso- and 4-nitropyrazoles with complex metal hydrides and organometallic reagents. Furthermore, 4-nitropyrazolium tetrafluoroborates are reactive substrates towards organolithium and Grignard compounds leading to new and highly substituted 4-nitro-3-pyrazolines and 4-nitropyrazolidines. The formation of 3-pyrazolines is regioselective

  2-吡唑啉-4-肟是通过4-亚硝基和4-硝基吡唑与复杂的金属氢化物和有机金属试剂的反应合成的。此外，4-硝基吡唑鎓四氟硼酸盐是有机锂和格氏试剂的反应性底物，从而导致新的和高度取代的4-硝基-3-吡唑啉和4-硝基吡唑烷。3-吡唑啉的形成是区域选择性的，并且当可能存在非对映异构体吡唑烷时，仅获得最稳定的3,4-反式和/或4,5-反式异构体。
• Highly diastereoselective Heck–Matsuda reaction with pyrazolyl diazonium salts
  作者：F. Bellina、F. Berti、S. M. Bertozzi、T. Bandiera、F. Bertozzi

  DOI：10.1039/d3nj01724a

  日期：——

  The Heck–Matsuda (HM) reaction is a powerful synthetic approach cut out for C–C bonds formation under mild conditions. We demonstrated that pyrazolyl diazonium salts are suitable reagents in this protocol, allowing us to deliver highly substituted cyclopentenols and cyclopentenamines with an excellent degree of diastereoselectivity and a control of enantioselectivity.

  Heck-Matsuda (HM) 反应是一种强大的合成方法，适合在温和条件下形成 C-C 键。我们证明了吡唑基重氮盐是该协议中的合适试剂，使我们能够提供高度取代的环戊烯醇和环戊烯胺，具有出色的非对映选择性和对映选择性控制。
• Depsipeptides Featuring a Neutral P1 Are Potent Inhibitors of Kallikrein-Related Peptidase 6 with On-Target Cellular Activity
  作者：Elena De Vita、Peter Schüler、Scott Lovell、Jasmin Lohbeck、Sven Kullmann、Eitan Rabinovich、Amiram Sananes、Bernd Heßling、Veronique Hamon、Niv Papo、Jochen Hess、Edward W. Tate、Nikolas Gunkel、Aubry K. Miller

  DOI：10.1021/acs.jmedchem.8b01106

  日期：2018.10.11

  Kallikrein-related peptidase 6 (KLK6) is a secreted serine protease that belongs to the family of tissue kallikreins (KLKs). Many KLKs are investigated as potential biomarkers for cancer as well as therapeutic drug targets for a number of pathologies. KLK6, in particular, has been implicated in neurodegenerative diseases and cancer, but target validation has been hampered by a lack of selective inhibitors. This work introduces a class of depsipeptidic KLK6 inhibitors, discovered via high-throughput screening, which were found to function as substrate mimics that transiently acylate the catalytic serine of KLK6. Detailed structure-activity relationship studies, aided by in silico modeling, uncovered strict structural requirements for potency, stability, and acyl-enzyme complex half-life. An optimized scaffold, DKFZ-251, demonstrated good selectivity for KLK6 compared to other KLKs, and on-target activity in a cellular assay. Moreover, DKFZ-633, an inhibitor-derived activity based probe, could be used to pull down active endogenous KLK6.
• Bernard, Polish Journal of Chemistry, 2001, vol. 75, # 10, p. 1465 - 1474
  作者：Bernard

  DOI：——

  日期：——
• HETERO-HALO INHIBITORS OF HISTONE DEACETYLASE
  申请人：Rodin Therapeutics, Inc.

  公开号：US20180194769A1

  公开（公告）日：2018-07-12

  This invention provides compounds that are inhibitors of HDAC2. The compounds (e.g., compounds according to Formula I, II or any of Compounds 100-128 or any of those in Tables 2 or 3) accordingly are useful for treating, alleviating, or preventing a condition in a subject such as a neurological disorder, memory or cognitive function disorder or impairment, extinction learning disorder, fungal disease or infection, inflammatory disease, hematological disease, or neoplastic disease, or for improving memory or treating, alleviating, or preventing memory loss or impairment.