(3,3-dimethylallyl)halfordinol | 17190-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3,3-dimethylallyl)halfordinol
• 英文别名: 5-(4-[(3-methylbut-2-en-1-yl)oxy]phenyl)-2-(pyridin-3-yl)oxazole；O-3,3(Dimethylallyl)halfordinol；Nicotinamid-O-dimethylallyl-halfordinol；3-{5-[4-(3-methyl-but-2-enyloxy)-phenyl]-oxazol-2-yl}-pyridine；Pyridine, 3-[5-[4-[(3-methyl-2-butenyl)oxy]phenyl]-2-oxazolyl]-；5-[4-(3-methylbut-2-enoxy)phenyl]-2-pyridin-3-yl-1,3-oxazole
• CAS: 17190-80-6
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: CPMFTHYYYPZYOB-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  493.9±55.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  48.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(4-甲氧基苯基)噁唑 在 copper(l) iodide 、 三溴化硼 、 sodium hydride 、 sodium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.08h， 生成 (3,3-dimethylallyl)halfordinol
  参考文献：
  名称：

  Structure–Activity Relationships of New Natural Product-Based Diaryloxazoles with Selective Activity against Androgen Receptor-Positive Breast Cancer Cells

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.7b01228

文献信息

• Anti-adipogenic action of a novel oxazole derivative through activation of AMPK pathway
  作者：Tripti Mishra、Sanchita Gupta、Prashant Rai、Nilesh Khandelwal、Mohit Chourasiya、Vinita Kushwaha、Astha Singh、Salil Varshney、Anil Nilkanth Gaikwad、Tadigoppula Narender

  DOI：10.1016/j.ejmech.2023.115895

  日期：2023.12

  other environmental factors. Both natural and synthetic heterocyclic compounds, especially oxazoles, represent an interesting group of compounds and have gained much attention due to their remarkable biological activities. Therefore, a library of 3,3-DMAH (3,3-dimethylallylhalfordinol) inspired N-alkylated oxazole bromide salts with varied substitutions were prepared and screened using the 3T3-L1 model

  肥胖是一种慢性疾病，其病因有多种，包括遗传、医学、饮食和其他环境因素。天然和合成的杂环化合物，尤其是恶唑，代表了一组有趣的化合物，并因其显着的生物活性而受到广泛关注。因此，利用叙利亚金仓鼠脂肪生成的3T3-L1模型和HFD诱导的肥胖模型，制备并筛选了具有不同取代基的3,3-DMAH（3,3-二甲基烯丙基氟啶醇）启发的N-烷基化恶唑溴化盐文库。合成系列中的几种化合物对 3T3-L1 前脂肪细胞的分化表现出显着的抗脂肪形成潜力。化合物19e显示出所有化合物中最有效的活性，并被选择用于进一步研究。化合物19e抑制3T3-L1细胞的有丝分裂克隆扩张，并通过AMPK激活提高分化早期细胞的线粒体耗氧率。19e还改善了高热量饮食喂养的叙利亚金仓鼠的血脂异常。因此，化合物19e可以作为对抗脂肪生成和血脂异常模型的潜在先导物质，并且可以进一步研究以确认其作为候选药物的重要性。
• 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.

表征谱图