4-[2-(3-吡啶基)-5-恶唑基]苯酚 | 4210-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-[2-(3-吡啶基)-5-恶唑基]苯酚
• 英文名称: halfordinol
• 英文别名: 4-(2-pyridin-3-yl-oxazol-5-yl)-phenol；4-(2-[3]pyridyl-oxazol-5-yl)-phenol；Aegelenin(=Halfordinol)；Malfordinol；aegelenine；4-(2-pyridin-3-yl-1,3-oxazol-5-yl)phenol
• CAS: 4210-82-6
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: FUXBKWOAAPDDGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 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：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	O-methylhalfordinol	33864-03-8	C15H12N2O2	252.272
  ——	O-Benzyl-halfordinol	4195-29-3	C21H16N2O2	328.37
  ——	Halfordin	4674-98-0	C19H20N2O4	340.379

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	O-methylhalfordinol	33864-03-8	C15H12N2O2	252.272
  ——	Acetylaegelenin	33864-02-7	C16H12N2O3	280.283
  ——	(3,3-dimethylallyl)halfordinol	17190-80-6	C19H18N2O2	306.364
  ——	(E)-5-(4-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]phenyl)-2-(pyridin-3-yl)oxazole	89764-17-0	C24H26N2O2	374.483

反应信息

• 作为反应物：
  描述：

  4-[2-(3-吡啶基)-5-恶唑基]苯酚 在 碘甲烷 作用下， 生成 Aegelenin-methiodid
  参考文献：
  名称：

  Crow,W.D.; Hodgkin,J.H., Australian Journal of Chemistry, 1964, vol. 17, p. 119 - 129

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Methyl-halfordinium 在 硫酸 作用下， 100.0~190.0 ℃ 、26.66 Pa 条件下， 反应 5.0h， 生成 4-[2-(3-吡啶基)-5-恶唑基]苯酚
  参考文献：
  名称：

  Crow,W.D.; Hodgkin,J.H., Australian Journal of Chemistry, 1964, vol. 17, p. 119 - 129

  摘要：

  DOI：

文献信息

• Practical oxazole synthesis mediated by iodine from α-bromoketones and benzylamine derivatives
  作者：Wen-Chao Gao、Ruo-Lin Wang、Chi Zhang

  DOI：10.1039/c3ob41566j

  日期：——

  system of I2/K2CO3 could efficiently promote the oxazole synthesis from α-bromoketones and benzylamine derivatives in DMF. This method was not only suitable for 2,5-diaryl oxazole synthesis but also for 2,4,5-trisubstituted oxazole and 5-alkyl/alkenyl oxazole synthesis. Furthermore, this method was successfully applied to a one-step synthesis of a natural product halfordinol in 62% yield.

  I 2 / K 2 CO 3试剂体系可有效促进DMF中α-溴代酮和苄胺衍生物的恶唑合成。该方法不仅适用于2，5-二芳基恶唑的合成，而且适用于2，4，5-三取代的恶唑和5-烷基/烯基恶唑的合成。此外，该方法已成功地以62％的收率成功地一步合成了天然产物Halfordinol。
• Structure–Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells
  作者：Andrew J. Robles、Shelby McCowen、Shengxin Cai、Michaels Glassman、Francisco Ruiz、Robert H. Cichewicz、Stanton F. McHardy、Susan L. Mooberry

  DOI：10.1021/acs.jmedchem.7b01228

  日期：2017.11.22

  Targeted therapies for ER+/PR+ and HER2-amplified breast cancers have improved patient survival, but there are no therapies for triple negative breast cancers (TNBC) that lack expression of estrogen and progesterone receptors (ER/PR), or amplification or overexpression of HER2. Gene expression profiling of TNBC has identified molecular subtypes and representative cell lines. An extract of the Texas native plant Amyris texana was found to have selective activity against MDA-MB-453 cells, a model of the luminal androgen receptor (LAR) subtype of TNBC. Bioassay-guided fractionation identified two oxazole natural products with selective activity against this cell line. Conducted analog synthesis and structure activity relationship studies provided analogs with more potent and selective activity against two LAR. subtype cell line models, culminating in the discovery of compound 30 (CIDD-0067106). Lead compounds discovered have potent and selective antiproliferative activities, and mechanisms of action studies show they inhibit the activity of the mTORC1 pathway.
• Chatterjee,A.; Majumder,R., Indian Journal of Chemistry, 1971, vol. 9, p. 763 - 766
  作者：Chatterjee,A.、Majumder,R.

  DOI：——

  日期：——
• Brossi,A.; Wenis,E., Journal of Heterocyclic Chemistry, 1965, vol. 2, p. 310 - 312
  作者：Brossi,A.、Wenis,E.

  DOI：——

  日期：——
• Alkaloids of the Australian rutaceae: halfordia scleroxyla.
  作者：W.D. Crow、J.H. Hodgkin

  DOI：10.1016/s0040-4039(01)90583-0

  日期：——