1-仲-丁基-1H-咪唑-2-甲醛 | 497855-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-仲-丁基-1H-咪唑-2-甲醛
• 英文名称: 1-(sec-butyl)-1H-imidazole-2-carbaldehyde
• 英文别名: 1-sec-butyl-1H-imidazole-2-carbaldehyde；1-(2-butyl)imidazole-2-carboxyaldehyde；1-Butan-2-ylimidazole-2-carbaldehyde
• CAS: 497855-78-4
• 化学式: C₈H₁₂N₂O
• mdl: MFCD09908555
• 分子量: 152.196
• InChiKey: YQRBJUZFYJOBOK-UHFFFAOYSA-N

物化性质

• 沸点：
  267.4±23.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-仲-丁基-1H-咪唑-2-甲醛 在 lithium aluminium tetrahydride 、 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (1-仲-丁基-1H-咪唑-2-基)甲醇盐酸盐(1:1)
  参考文献：
  名称：

  BENZAZEPINE DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND USE

  摘要：

  本发明提供了一种新型的苯并氮杂环衍生物，其由以下公式表示： 其中，R1是一个5-或6-成员的芳香环，R2是低级烷基团等，Y是可选地取代的亚氨基，环A和环B是独立地选自一个可选地取代的芳香环，W是公式-W1-X2-W2-（W1和W2是独立地为S(O)m1（m1是0、1或2）等，X2是一个可选地取代的亚烷基团等），其制备方法及其用途。

  公开号：

  EP1422228A1
• 作为产物：
  描述：

  2-溴丁烷 、 2-咪唑甲醛 在 potassium carbonate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 6.0h， 生成 1-仲-丁基-1H-咪唑-2-甲醛
  参考文献：
  名称：

  BENZAZEPINE DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND USE

  摘要：

  本发明提供了一种新型的苯并氮杂环衍生物，其由以下公式表示： 其中，R1是一个5-或6-成员的芳香环，R2是低级烷基团等，Y是可选地取代的亚氨基，环A和环B是独立地选自一个可选地取代的芳香环，W是公式-W1-X2-W2-（W1和W2是独立地为S(O)m1（m1是0、1或2）等，X2是一个可选地取代的亚烷基团等），其制备方法及其用途。

  公开号：

  EP1422228A1

文献信息

• Design, synthesis, and biological evaluation of 1,9-diheteroarylnona-1,3,6,8-tetraen-5-ones as a new class of anti-prostate cancer agents
  作者：Xiaojie Zhang、Rubing Wang、German Ruiz Perez、Guanglin Chen、Qiang Zhang、Shilong Zheng、Guangdi Wang、Qiao-Hong Chen

  DOI：10.1016/j.bmc.2016.08.006

  日期：2016.10

  inhibiting prostate cancer cell proliferation. It can be concluded from our data that 1,9-diarylnona-1,3,6,8-tetraen-5-one can serve as a new potential scaffold for the development of anti-prostate cancer agents and that pyridine-4-yls and quinolin-4-yl act as optimal heteroaromatic rings for the enhanced potency of this scaffold. Two of the most potent compounds, 68 and 75, effectively suppress PC-3 cell

  为了寻求更有效的化学疗法来治疗去势抵抗性前列腺癌并受到姜黄素类似物的启发，二十五个（1 E，3 E，6 E，8 E）-1,9-diarylnona-1,3,6,8通过Wittig反应，然后进行Horner-Wadsworth-Emmons反应，已成功合成了带有两个相同末端杂芳族环的-tetraen-5-ones。其中的二十三种是新化合物。WST-1细胞增殖测定法用于评估其对雄激素敏感性和雄激素敏感性人类前列腺癌细胞系的抗增殖作用。与姜黄素相比，二十五个合成化合物中有十八个具有显着改善的效能。最佳化合物78在抑制前列腺癌细胞增殖方面，β-内啡肽的活性比姜黄素高14到23倍。从我们的数据可以得出结论，1,9-二芳基壬娜-1,3,6,8-四烯基5-one可以作为开发抗前列腺癌药物和吡啶-4-基的新的潜在支架。和喹啉-4-基充当最佳杂芳环，以增强该支架的效能。两种最有效的化合物68和75通过激活细胞凋亡和将细胞周期阻滞在G
• Benzazepine derivative, process for producing the same, and use
  申请人：——

  公开号：US20040235822A1

  公开（公告）日：2004-11-25

  The present invention provides a novel benzazepine derivative represented by formula: 1 wherein, R 1 is a 5- or 6-membered aromatic ring, R 2 is lower alkyl group, etc., Y is an optionally substituted imino group, ring A and ring B are independently an optionally substituted aromatic ring, W is formula —W 1 —X 2 —W 2 — (W 1 and W 2 are independently S(O) m1 (m1 is 0, 1, or 2), etc., and X 2 is an optionally substituted alkylene group etc.), a preparation method and use thereof.

  本发明提供了一种新型苯并氮杂环衍生物，其化学式表示为：1其中，R1为5-或6-成员芳香环，R2为低碳基，Y为可选取代的亚胺基，环A和环B分别为可选取代的芳香环，W为式—W1—X2—W2—（其中W1和W2分别为独立的S(O)m1（m1为0、1或2）等，X2为可选取代的烷基等），以及其制备方法和用途。
• Asymmetric 1,5-diarylpenta-1,4-dien-3-ones: Antiproliferative activity in prostate epithelial cell models and pharmacokinetic studies
  作者：Xiaojie Zhang、Shanchun Guo、Chengsheng Chen、German Ruiz Perez、Changde Zhang、Manee Patanapongpibul、Nithya Subrahmanyam、Rubing Wang、Joshua Keith、Guanglin Chen、Yan Dong、Qiang Zhang、Qiu Zhong、Shilong Zheng、Guangdi Wang、Qiao-Hong Chen

  DOI：10.1016/j.ejmech.2017.05.062

  日期：2017.9

  To further engineer dienones with optimal combinations of potency and bioavailability, thirty-four asymmetric 1,5-diarylpenta-1,4-dien-3-ones (25-58) have been designed and synthesized for the evaluation of their in vitro anti-proliferative activity in three human prostate cancer cell lines and one non-neoplastic prostate epithelial cell line. All these asymmetric dienones are sufficiently more potent than curcumin and their corresponding symmetric counterparts. The optimal dienone 58, with IC50 values in the range of 0.03-0.12 mu M, is 636-, 219-, and 454-fold more potent than curcumin in three prostate cancer cell models. Dienones 28 and 49 emerged as the most promising asymmetric dienones that warrant further preclinical studies. The two lead compounds demonstrated substantially improved potency in cell models and superior bioavailability in rats, while exhibiting no acute toxicity in the animals at the dose of 10 mg/kg. Dienones 28 and 46 can induce PC-3 cell cycle regulation at the G(0)/G(1) phase. However, dienone 28 induces PC-3 cell death in a different way from 46 even though they share the same scaffold, indicating that terminal heteroaromatic rings are critical to the action of mechanism for each specific dienone. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Structure-activity relationship studies of 1,7-diheteroarylhepta-1,4,6-trien-3-ones with two different terminal rings in prostate epithelial cell models
  作者：Rubing Wang、Xiaojie Zhang、Chengsheng Chen、Guanglin Chen、Cristian Sarabia、Qiang Zhang、Shilong Zheng、Guangdi Wang、Qiao-Hong Chen

  DOI：10.1016/j.ejmech.2017.03.067

  日期：2017.6

  To systematically investigate the structure-activity relationships of 1,7-diarylhepta-1,4,6-trien-3-ones in three human prostate cancer cell models and one human prostate non-neoplastic epithelial cell model, thirty five 1,7-diarylhepta-1,4,6-trien-3-ones with different terminal heteroaromatic rings have been designed for evaluation of their anti-proliferative potency in vitro. These target compounds have been successfully synthesized through two sequential Horner-Wadsworth-Emmons reactions starting from the appropriate aldehydes and tetraethyl (2-oxopropane-1,3-diyl)bis(phosphonate). Their anti-proliferative potency against PC-3, DU-145 and LNCaP human prostate cancer cell lines can be significantly enhanced by the manipulation of the terminal heteroaromatic rings, further demonstrating the utility of 1,7-diarylhepta-1,4,6-trien-3-one as a potential scaffold for the development of anti prostate cancer agents. The optimal analog 40 is 82-, 67-, and 39-fold more potent than curcumin toward the three prostate cancer cell lines, respectively. The experimental data also reveal that the trienones with two different terminal aromatic rings possess greater potency toward three prostate cancer cell lines, but also have greater capability of suppressing the proliferation of PWR-1E benign human prostate epithelial cells, as compared to the corresponding counterparts with two identical terminal rings and curcumin. The terminal aromatic rings also affect the cell apoptosis perturbation. (C) 2017 Elsevier Masson SAS. All rights reserved.
• A new class of hybrid anticancer agents inspired by the synergistic effects of curcumin and genistein: Design, synthesis, and anti-proliferative evaluation
  作者：Qiao-Hong Chen、Kevin Yu、Xiaojie Zhang、Guanglin Chen、Andrew Hoover、Francisco Leon、Rubing Wang、Nithya Subrahmanyam、Ermias Addo Mekuria、Liva Harinantenaina Rakotondraibe

  DOI：10.1016/j.bmcl.2015.08.064

  日期：2015.10

  Inspired by the synergistic effects of dietary natural products with different scaffolds on the inhibition of cancer cell proliferation, incorporation of central (1E, 4E)-1,4-penta-dien-3-one linker (an optimal substitute for the central metabolically unstable diketone linker of curcumin), 1-alkyl-1H-imidazol-2-yl (a promising bioisostere of terminal aryl group in curcumin), and chromone (the common pharmacophore in genistein and quercetin) into one chemical entity resulted in ten new hybrid molecules, 3-((1E, 4E)-5-(1-alkyl-1H-imidazol-2-yl)-3-oxopenta-1,4-dien-1-yl)-4H-chromen-4-ones. They were synthesized through a three-step transformation using acid-catalyzed aldol condensation as key step. The WST-1 cell proliferation assay showed that they have greater anti-proliferative potency than curcumin, quercetin, and genistein on both androgen-dependent and androgen-independent human prostate cancer cells. Published by Elsevier Ltd.