3-mercapto-5,6-diphenylpyridazine | 13035-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-mercapto-5,6-diphenylpyridazine
• 英文别名: 5,6-diphenyl-3(2H)pyridazinethione；3-Mercapto-5,6-diphenyl-pyridazin；5.6-Diphenyl-3(2H)-thionopyridazin；5,6-diphenyl-2H-pyridazine-3-thione；3,4-diphenyl-1H-pyridazine-6-thione
• CAS: 13035-78-4
• 化学式: C₁₆H₁₂N₂S
• 分子量: 264.351
• InChiKey: UZOSYUWFZOJMHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-mercapto-5,6-diphenylpyridazine 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-(5,6-Diphenyl-pyridazin-3-ylsulfanyl)-hexanoic acid
  参考文献：
  名称：

  5,6-二苯基哒嗪衍生物作为酰基辅酶A：胆固醇酰基转移酶抑制剂。

  摘要：

  合成并测试了结合了ACAT抑制剂几个主要特征的烷基5,6-二苯基哒嗪衍生物，例如与杂环和邻二苯基系统相连的长烷基侧链。此外，进行了具有代表性的术语的建模研究。从鼠肝微粒体分离的酶和鼠巨噬细胞的无细胞匀浆中，有些化合物在微摩尔范围内均表现出ACAT抑制作用。

  DOI：

  10.1021/jm010807h
• 作为产物：
  描述：

  5,6-二(苯基)-2H-哒嗪-3-酮 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以60%的产率得到3-mercapto-5,6-diphenylpyridazine
  参考文献：
  名称：

  Mono- or Diphenylpyridazines Connected to N-(2,4-Difluorophenyl)-N‘-heptylurea as Acyl-CoA:Cholesterol Acyltransferase Inhibitors

  摘要：

  Mono- and diphenylpyridazine ureido derivatives, structurally related to DuP 128, were synthesized and tested for their inhibitory activity against ACAT isolated from rat liver microsomes. Several compounds displayed ACAT inhibition in the micromolar range. The amino derivatives 4a-c were also tested against hACAT-1 and hACAT-2 isoforms. They retained the same trend shown in the previous assay. Modeling studies on representative terms were performed. Significant similarities between the geometrical features of the model DuP 128 and the most active pyridazine derivatives were observed.

  DOI：

  10.1021/jm050703x

文献信息

• Nonprostanoid prostacyclin mimetics. 3. Structural variations of the diphenyl heterocycle moiety
  作者：Nicholas A. Meanwell、Michael J. Rosenfeld、Ashok K. Trehan、Jeffrey L. Romine、J. J. Kim Wright、Catherine L. Brassard、John O. Buchanan、Marianne E. Federici、J. Stuart Fleming、Marianne Gamberdella、George B. Zavoico、Steven M. Seiler

  DOI：10.1021/jm00097a007

  日期：1992.9

  4,5-Diphenyl-2-oxazolenonanoic acid (2) and 2-[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetic acid (3) were previously identified as nonprostanoid prostacyclin (PGI2) mimetics that inhibit ADP-induced aggregation of human platelets in vitro. The effects on biological activity of substitution and structural modification of the 4- and 5-phenyl rings of 3 was examined. Potency showed a marked sensitivity

  4,5-二苯基-2-恶唑壬酸（2）和2- [3- [2-（4,5-二苯基-2-恶唑基）乙基]苯氧基]乙酸（3）先前被确定为非前列腺素前列环素（PGI2 ）在体外抑制ADP诱导的人类血小板聚集的模拟物。考察了3的4-和5-苯基环对取代和结构修饰的生物活性的影响。效能显示出对将取代基引入这些芳族环的显着敏感性，并且只有双-4-甲基衍生物9j（IC50 = 0.34 microM）与母体结构3（IC50 = 1.2 microM）相比具有增强的效能。在苯环的邻位或间位取代，被噻吩基或环己基部分取代，或限制在平面菲系统中产生的化合物不是ADP诱导的血小板聚集的有效抑制剂。相比之下，杂环部分的变化表明，SAR的严格性要低得多，并且发现许多5和6元杂环可有效替代2和3的恶唑环。二苯甲基部分可作为4,5-的有效等排体自13aad以来的二苯环杂环化合物显示出与3相似的血小板抑制活性。除了3,4,5-三苯基吡唑衍生物13g以外，与类似取代的3
• Synthesis and antiviral screening of some novel pyridazine and triazolopyridazine nucleosides
  作者：Aymn E. Rashad、Ahmed H. Shamroukh、Mohamed A. Ali、Faiza M. Abdel-Motti

  DOI：10.1002/hc.20296

  日期：2007.4

  Some novel cyclic and acyclic pyridazine and triazolopyridazine nucleoside derivatives were prepared. Some of the prepared products were selected and tested for antiviral activity against herpes simplex virus type-1 (HSV-1) and hepatitis-A virus (HAV, MBB-cell culture adapted strain). Plaque reduction infectivity assay was used to determine virus count reduction as a result of treatment with test compounds

  制备了一些新型环状和非环状哒嗪和三唑并哒嗪核苷衍生物。选择了一些制备的产品并测试了对单纯疱疹病毒 1 型（HSV-1）和甲型肝炎病毒（HAV，MBB 细胞培养适应株）的抗病毒活性。噬斑减少感染性测定用于确定由于用测试化合物处理而导致的病毒计数减少。与其他测试化合物相比，化合物 15 对 HAV 的影响最大。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:274–282, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20296
• Pyridazine derivatives as novel acyl-coa:cholesterol acyltransferase (acat) inhibitors
  作者：Arianna Gelain

  DOI：10.1002/jhet.5570420306

  日期：2005.4

  Acyl-CoA:cholesterol acyltransferase (E.C.2.3.1.26, ACAT) is a microsomial enzyme that catalyses the formation of cholesteryl esters by acylation of cholesterol with long chain fatty acylCoA [1].

  酰基辅酶A：胆固醇酰基转移酶（EC2.3.1.26，ACAT）是一种微粒体酶，可通过将胆固醇与长链脂肪酰基辅酶A酰化来催化胆固醇酯的形成[1]。
• Ureidopyridazine Derivatives as Acyl-CoA: cholesterol acyltransferase Inhibitors
  作者：Arianna Gelain

  DOI：10.3797/scipharm.2006.74.85

  日期：——

  A series of N-(2,4-difluorophenyl)-N’-heptyl-N’-4-[(substituted)-pyridazin-3-yl)thio]pentyl}urea derivatives having a phenyl ring at positions 5 and/or at position 6 of the heterocycle, as well as the corresponding sulfones, were synthesized. Their inhibitory activity against acyl-CoA:cholesterol acyltransferase (ACAT) was tested on the enzyme prepared from rat liver microsomes. Theoretical studies were performed to correlate their activity to their structural features.

  我们合成了一系列 N-(2,4-二氟苯基)-N'-庚基-N'-4-[(取代的)-哒嗪-3-基)硫代]戊基}脲衍生物，这些衍生物的杂环第 5 位和/或第 6 位上有一个苯基环，我们还合成了相应的砜类化合物。在从大鼠肝脏微粒体制备的酶上测试了它们对酰基-CoA：胆固醇酰基转移酶（ACAT）的抑制活性。为了将它们的活性与其结构特征联系起来，还进行了理论研究。
• Motti, F. M. Abdel; Sayed, H. H.; Shamroukh, A. H., Egyptian Journal of Chemistry, 2002, vol. 45, # 6, p. 1123 - 1132
  作者：Motti, F. M. Abdel、Sayed, H. H.、Shamroukh, A. H.、Abdel-Megeid, F. M. E.

  DOI：——

  日期：——