5-(2-naphthyl)furan-2-carbaldehyde | 51792-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(2-naphthyl)furan-2-carbaldehyde
• 英文别名: 5-(Naphthalen-2-yl)furan-2-carbaldehyde；5-naphthalen-2-ylfuran-2-carbaldehyde
• CAS: 51792-37-1
• 化学式: C₁₅H₁₀O₂
• mdl: MFCD02812466
• 分子量: 222.243
• InChiKey: PWOCSPAWPUQFAD-UHFFFAOYSA-N

物化性质

• 熔点：
  106 °C(Solv: ethanol (64-17-5))
• 沸点：
  234-240 °C(Press: 2 Torr)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 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：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(2-naphthyl)furan-2-carbaldehyde 在 哌啶 、 吡啶 、 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 (E)-N-[3-benzoyl-4-[[2-(4-methylphenyl)acetyl]amino]phenyl]-3-(5-naphthalen-2-ylfuran-2-yl)prop-2-enamide
  参考文献：
  名称：

  非硫醇法呢基转移酶抑制剂：N-（4-甲苯基乙酰氨基-3-苯甲酰基苯基）-3-芳基呋喃基丙烯酸酰胺。

  摘要：

  我们已经设计了芳基呋喃基丙烯酸取代的二苯甲酮作为非硫醇法呢基转移酶抑制剂，利用了法呢基转移酶的新型芳基结合位点。这些化合物在低纳摩尔范围内显示活性。

  DOI：

  10.1016/j.bmc.2004.07.010
• 作为产物：
  描述：

  2-萘胺 在 盐酸 、 copper dichloride 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 13.0h， 生成 5-(2-naphthyl)furan-2-carbaldehyde
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of furan derivatives bearing a rhodanine moiety

  摘要：

  Two series of furan derivatives bearing a rhodanine moiety (4a-l and 5a-l) have been synthesized, characterized, and evaluated for their antibacterial activity. The majority of these compounds showed potent levels of inhibitory activity against a variety of different Gram-positive bacteria, including multidrug-resistant clinical isolates, with minimum inhibitory concentration (MIC) values in the range of 2-16 mu g/mL. In particular, compound 4l was found to be the most potent of the synthesized compounds against the multidrug-resistant strains, with a MIC value of 2 or 4 mu g/mL. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. An examination of the cytotoxicities of these agents revealed that they displayed low levels of toxicity toward HeLa cells. All of the compounds synthesized in the current paper were characterized by H-1 and C-13 NMR, infrared, and mass spectroscopy.

  DOI：

  10.1007/s00044-013-0648-7

文献信息

• 5-Aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety as potential PTP1B inhibitors
  作者：Tianwei Niu、Peipei Wang、Cheng Li、Tong Dou、Huri Piao、Jia Li、Liangpeng Sun

  DOI：10.1016/j.bioorg.2020.104483

  日期：2021.1

  Two series of 5-aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, 5g was found to have the best PTP1B inhibitory potency (IC50 = 2.66 ± 0.16 µM) and the best cell division cycle 25 homolog B (CDC25B) inhibitory potency (IC50 = 0.25 ± 0.02 µM). Enzymatic

  两个系列带有苯丙氨酸或异亮氨酸衍生的罗丹宁部分的 5-芳基-呋喃衍生物被鉴定为竞争性蛋白酪氨酸磷酸酶 1B (PTP1B) 抑制剂。在研究的化合物中，发现5g具有最佳的 PTP1B 抑制效力（IC 50 = 2.66 ± 0.16 µM）和最佳的细胞分裂周期 25 同源物 B (CDC25B) 抑制效力（IC 50 = 0.25 ± 0.02 µM）。酶学数据和分子建模结果表明，在羧基的 2-位引入仲丁基显着提高了 PTP1B 抑制活性。
• Development of a novel class of B-RafV600E-selective inhibitors through virtual screening and hierarchical hit optimization
  作者：Xiangqian Kong、Jie Qin、Zeng Li、Adina Vultur、Linjiang Tong、Enguang Feng、Geena Rajan、Shien Liu、Junyan Lu、Zhongjie Liang、Mingyue Zheng、Weiliang Zhu、Hualiang Jiang、Meenhard Herlyn、Hong Liu、Ronen Marmorstein、Cheng Luo

  DOI：10.1039/c2ob26081f

  日期：——

  Oncogenic mutations in critical nodes of cellular signaling pathways have been associated with tumorigenesis and progression. The B-Raf protein kinase, a key hub in the canonical MAPK signaling cascade, is mutated in a broad range of human cancers and especially in malignant melanoma. The most prevalent B-RafV600E mutant exhibits elevated kinase activity and results in constitutive activation of the MAPK pathway, thus making it a promising drug target for cancer therapy. Herein, we describe the development of novel B-RafV600E selective inhibitors via multi-step virtual screening and hierarchical hit optimization. Nine hit compounds with low micromolar IC50 values were identified as B-RafV600E inhibitors through virtual screening. Subsequent scaffold-based analogue searching and medicinal chemistry efforts significantly improved both the inhibitor potency and oncogene selectivity. In particular, compounds 22f and 22q possess nanomolar IC50 values with selectivity for B-RafV600Ein vitro and exclusive cytotoxicity against B-RafV600E harboring cancer cells.

  细胞信号通路关键节点的致癌突变与肿瘤的发生和发展有关。B-Raf蛋白激酶是典型MAPK信号级联的关键枢纽，在多种人类癌症，尤其是恶性黑色素瘤中发生突变。最常见的B-RafV600E突变体表现出较高的激酶活性，导致MAPK通路的组成性激活，从而使其成为一种很有希望的癌症治疗药物靶点。在此，我们介绍了通过多步虚拟筛选和分层命中优化开发新型 B-RafV600E 选择性抑制剂的情况。通过虚拟筛选，我们确定了九种具有低微摩尔 IC50 值的命中化合物作为 B-RafV600E 抑制剂。随后的基于支架的类似物搜索和药物化学工作显著提高了抑制剂的效力和对癌基因的选择性。其中，22f 和 22q 化合物的 IC50 值达到纳摩尔级，在体外对 B-RafV600E 具有选择性，对携带 B-RafV600E 的癌细胞具有独特的细胞毒性。
• Heterocyclic guanidines AS 5HT 3 Antagonists
  申请人：PFIZER INC.

  公开号：EP0397364A1

  公开（公告）日：1990-11-14

  Heterocyclicguanidines as 5HT₃ antagonists useful in the treatment of nausea, anxiety, pain, schizophrenia and gastrointestinal disorders, of the formula and their pharmaceutically acceptable acid addition salts, wherein Ar is naphthyl, indol-3-yl, 2-methyl-indol-3-yl, 1-methylindol-3-yl, 1-benzylindol-3-yl, phenyl, or mono- or disubstituted phenyl wherein said substituent is each methyl, methoxy, chloro, fluoro or bromo; Het is thiazolyl, furyl, thienyl or isoxazolyl, R₁ is hydrogen or methyl; R₂ and R₃ when considered separately are each hydrogen, hydroxyethyl, alkyl having one to six carbon atoms, cycloalkyl having three to six carbon atoms or acetyl; and R₂ and R₃ when taken together are alkylene having two to three carbon atoms.

  作为 5HT₃ 拮抗剂，可用于治疗恶心、焦虑、疼痛、精神分裂症和胃肠道疾病的杂环胍类化合物，其式为 及其药学上可接受的酸加成盐，其中 Ar 为萘基、吲哚-3-基、2-甲基吲哚-3-基、1-甲基吲哚-3-基、1-苄基吲哚-3-基、苯基或单取代或二取代苯基，其中所述取代基分别为甲基、甲氧基、氯代、氟代或溴代；Het 是噻唑基、呋喃基、噻吩基或异噁唑基，R₁ 是氢或甲基；R₂ 和 R₃ 分开看分别是氢、羟乙基、具有 1 至 6 个碳原子的烷基、具有 3 至 6 个碳原子的环烷基或乙酰基；R₂ 和 R₃ 合在一起看是具有 2 至 3 个碳原子的亚烷基。
• Obushak, N. D.; Lesyuk, A. I.; Ganushchak, N. I., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 11, p. 2093 - 2097
  作者：Obushak, N. D.、Lesyuk, A. I.、Ganushchak, N. I.、Mel'nik, G. M.、Zavalii, P. Yu.

  DOI：——

  日期：——
• Preparation of 5-Aryl Furfurals and Aryl Thiophene-2-carboxaldehydes via Palladium-Catalyzed C−C Bond Formation in Aqueous Media¹
  作者：Jacqueline C. Bussolari、Diana C. Rehborn

  DOI：10.1021/ol990708m

  日期：1999.10.1

  [GRAPHICS]A series of 5-aryl furfurals and aryl thiophene-2-carboxaldehydes was synthesized. To this end, efficient and effective palladium-catalyzed C-C bond-forming reactions were carried out at room temperature in aqueous media. This mild process allowed the cross-coupling reaction of the bromides to occur in the presence of electrophilic functional groups, which is a valuable advantage over previously reported methods.