4-benzoyl-3-methyl-1-phenyl-2-pyrazoline-5-thione | 79071-33-3

• 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-benzoyl-3-methyl-1-phenyl-2-pyrazoline-5-thione
• 英文别名: 1-Phenyl-3-methyl-4-benzoyl-pyrazol-5-thion；1-phenyl-3-methyl-4-benzoylpyrazol-5-thione；4-benzoyl-3-methyl-1-phenylpyrazol-5-thiol；4-Benzoyl-3-methyl-1-phenyl-5-mercaptopyrazol；(3-methyl-1-phenyl-5-sulfanylpyrazol-4-yl)-phenylmethanone
• CAS: 79071-33-3
• 化学式: C₁₇H₁₄N₂OS
• 分子量: 294.377
• InChiKey: BHSACAHFKVJVSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.89
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-benzoyl-3-methyl-1-phenyl-2-pyrazoline-5-thione 在 羟胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (4Z)-4-[(hydroxyamino)-phenylmethylidene]-5-methyl-2-phenylpyrazole-3-thione
  参考文献：
  名称：

  Hennig, Lothar; Mann, Gerhard, Zeitschrift fur Chemie, 1988, vol. 28, # 10, p. 364 - 365

  摘要：

  DOI：
• 作为产物：
  描述：

  5-Chlor-3-Methyl-1-phenyl-4-benzoyl-pyrazol 在 sodiumsulfide nonahydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到4-benzoyl-3-methyl-1-phenyl-2-pyrazoline-5-thione
  参考文献：
  名称：

  Disulfide linked pyrazole derivatives inhibit phagocytosis of opsonized blood cells

  摘要：

  Immune thrombocytopenia (ITP) is caused by production of an autoantibody to autologous platelets. ITP can be treated either by reducing platelet destruction or by increasing platelet production. Fc gamma receptor mediated phagocytosis of the opsonized blood cells is a well-accepted mechanism for the underlying pathogenesis of ITP and inhibition of this phagocytosis process with small molecules is a potential strategy for the development of drugs against ITP. A broad screen indicated that 4-methyl-1-phenyl-pyrazole derivative (1) could inhibit the phagocytosis of opsonized blood cells with weak potency. We reveal here the discovery of the polysulfide products, synthesis of various 1-phenyl-pyrazole derivatives, and the biological evaluation of pyrazole derivatives as inhibitors of phagocytosis for potential use as therapeutics for ITP. Substitution at C4 of the pyrazole moiety in the disulfide-bridged dimers influenced the potency in the increasing order of 10 congruent to 11 congruent to 16 < 19 < 20. A novel scaffold, 20 with an IC50 of 100 nM inhibiting opsonized blood cell phagocytosis was identified as a potential candidate for further studies. Confirmation of the disulfide bridge additionally provides clues for the non-thiol or non-disulfide bridge carrying ligands targeting ITP and other similar disorders. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.064

文献信息

• Bechmann, W.; Uhlemann, E.; Kirmse, R., Zeitschrift fur Anorganische und Allgemeine Chemie
  作者：Bechmann, W.、Uhlemann, E.、Kirmse, R.、Koehler, K.

  DOI：——

  日期：——
• Synthesis of Novel Arylthio Derivatives of Mucochloric Acid
  作者：A. R. Kurbangalieva、N. F. Devyatova、A. V. Bogdanov、E. A. Berdnikov、T. G. Mannafov、D. B. Krivolapov、I. A. Litvinov、G. A. Chmutova

  DOI：10.1080/10426500601015989

  日期：2007.4.1

  Stable reaction products of mucochloric acid with aromatic and heterocyclic thiols were synthesized and characterized. Under basic conditions the reactions proceeded with the substitution of the chlorine atom(s) by arylthiogroup(s), while in an acidic medium the hydroxy group at C-5 was substituted. Different types of new sulfur-containing products of di- and trisubstitution on the basis of mucochloric acid were obtained. In one case a new acyclic product-di-p-tolyl-2,3-bis-(p-tolylthio)butanedithioate-was isolated. The structure of all synthesized compounds was confirmed by IR, H-1, and C-13 NMR spectroscopy; three compounds were characterized by single crystal X-ray diffraction.
• Knoblauch, Stephan; Benedix, Roland; Ecke, Martin, European Journal of Inorganic Chemistry, 1999, # 8, p. 1392 - 1404
  作者：Knoblauch, Stephan、Benedix, Roland、Ecke, Martin、Gelbrich, Thomas、Sieler, Joachim、Somoza, Fernando、Hennig, Horst

  DOI：——

  日期：——
• HENNIG, LOTHAR;MANN, GERHARD, Z. CHEM., 28,(1988) N 10, C. 364-365
  作者：HENNIG, LOTHAR、MANN, GERHARD

  DOI：——

  日期：——
• Disulfide linked pyrazole derivatives inhibit phagocytosis of opsonized blood cells
  作者：Meena K. Purohit、Iain Scovell、Anton Neschadim、Yulia Katsman、Donald R. Branch、Lakshmi P. Kotra

  DOI：10.1016/j.bmcl.2013.02.064

  日期：2013.4

  Immune thrombocytopenia (ITP) is caused by production of an autoantibody to autologous platelets. ITP can be treated either by reducing platelet destruction or by increasing platelet production. Fc gamma receptor mediated phagocytosis of the opsonized blood cells is a well-accepted mechanism for the underlying pathogenesis of ITP and inhibition of this phagocytosis process with small molecules is a potential strategy for the development of drugs against ITP. A broad screen indicated that 4-methyl-1-phenyl-pyrazole derivative (1) could inhibit the phagocytosis of opsonized blood cells with weak potency. We reveal here the discovery of the polysulfide products, synthesis of various 1-phenyl-pyrazole derivatives, and the biological evaluation of pyrazole derivatives as inhibitors of phagocytosis for potential use as therapeutics for ITP. Substitution at C4 of the pyrazole moiety in the disulfide-bridged dimers influenced the potency in the increasing order of 10 congruent to 11 congruent to 16 < 19 < 20. A novel scaffold, 20 with an IC50 of 100 nM inhibiting opsonized blood cell phagocytosis was identified as a potential candidate for further studies. Confirmation of the disulfide bridge additionally provides clues for the non-thiol or non-disulfide bridge carrying ligands targeting ITP and other similar disorders. (C) 2013 Elsevier Ltd. All rights reserved.