2-(benzo[d][1,3]dioxol-5-yl)-N-phenylacetamide | 96718-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(benzo[d][1,3]dioxol-5-yl)-N-phenylacetamide
• 英文别名: 2-(1,3-benzodioxol-5-yl)-N-phenylacetamide
• CAS: 96718-69-3
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: QFUKDACBARUZJU-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C(Solvent: Methanol)
• 沸点：
  487.6±24.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(benzo[d][1,3]dioxol-5-yl)-N-phenylacetamide 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氯化亚砜 、 potassium iodide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 为溶剂， 生成 5-(2-Fluoro-phenyl)-6-phenyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline
  参考文献：
  名称：

  Nagarajan, K.; Talwalker, P. K.; Kulkarni, C. L., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 83 - 97

  摘要：

  DOI：
• 作为产物：
  描述：

  胡椒乙酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 氯化亚砜 作用下， 以 乙醚 、 苯 为溶剂， 生成 2-(benzo[d][1,3]dioxol-5-yl)-N-phenylacetamide
  参考文献：
  名称：

  Nagarajan, K.; Talwalker, P. K.; Kulkarni, C. L., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 83 - 97

  摘要：

  DOI：

文献信息

• Direct Csp³–H methylenation of 2-arylacetamides using DMF/Me₂NH-BH₃ as the methylene source
  作者：Yuting Liu、Chang-Ling Wang、Hui-Min Xia、Zhijuan Wang、Yi-Feng Wang

  DOI：10.1039/c9ob00875f

  日期：——

  A direct Csp3–H methylenation of 2-arylacetamides using DMF/Me2NH-BH3 as the methylene source was developed. The formyl group of DMF delivered the carbon and one hydrogen atoms, and the Me2NH-BH3 donated the remaining one hydrogen atom. This protocol offers a new alternative to make useful 2-arylacrylamides from simple starting materials.

  开发了使用DMF / Me 2 NH-BH 3作为亚甲基源的2-芳基乙酰胺的直接Csp 3 -H亚甲基化反应。DMF的甲酰基传递了碳原子和一个氢原子，而Me 2 NH-BH 3则提供了剩余的一个氢原子。该协议为从简单的起始原料制备有用的2-芳基丙烯酰胺提供了新的选择。
• Characterization and Investigation of Novel Benzodioxol Derivatives as Antidiabetic Agents: An In Vitro and In Vivo Study in an Animal Model
  作者：Mohammed Hawash、Derar Al-Smadi、Anil Kumar、Barbara Olech、Paulina Maria Dominiak、Nidal Jaradat、Sarah Antari、Sarah Mohammed、Ala’a Nasasrh、Murad Abualhasan、Ahmed Musa、Shorooq Suboh、İrfan Çapan、Mohammad Qneibi、Hiba Natsheh

  DOI：10.3390/biom13101486

  日期：——

  In this study, we synthesized benzodioxol carboxamide derivatives and investigated their antidiabetic potential. The synthesized compounds (Ia-Ic and IIa-IId) underwent characterization via HRMS, 1H-, 13CAPT-NMR, and MicroED. Their efficacy against α-amylase was assessed in vitro, while MTS assays were employed to gauge cytotoxicity across cancer and normal cell lines. Additionally, the antidiabetic impact of compound IIc was evaluated in vivo using a streptozotocin-induced diabetic mice model. Notably, IIa and IIc displayed potent α-amylase inhibition (IC50 values of 0.85 and 0.68 µM, respectively) while exhibiting a negligible effect on the Hek293t normal cell line (IC50 > 150 µM), suggesting their safety. Compound IId demonstrated significant activity against four cancer cell lines (26–65 µM). In vivo experiments revealed that five doses of IIc substantially reduced mice blood glucose levels from 252.2 mg/dL to 173.8 mg/dL in contrast to the control group. The compelling in vitro anticancer efficacy of IIc and its safety for normal cells underscores the need for further in vivo assessment of this promising compound. This research highlights the potential of benzodioxol derivatives as candidates for the future development of synthetic antidiabetic drugs.

  在这项研究中，我们合成了苯并二恶茂羧酰胺衍生物，并研究了它们的抗糖尿病潜力。合成的化合物（Ia-Ic 和 IIa-IId）通过 HRMS、1H-、13CAPT-NMR 和 MicroED 进行了表征。它们对α-淀粉酶的功效在体外进行了评估，而 MTS 试验则用于衡量癌症和正常细胞系的细胞毒性。此外，还利用链脲佐菌素诱导的糖尿病小鼠模型对化合物 IIc 的抗糖尿病作用进行了体内评估。值得注意的是，IIa 和 IIc 对α-淀粉酶有很强的抑制作用（IC50 值分别为 0.85 和 0.68 µM），而对 Hek293t 正常细胞系的影响微乎其微（IC50 > 150 µM），这表明它们是安全的。化合物 IId 对四种癌症细胞株具有显著的活性（26-65 µM）。体内实验显示，与对照组相比，五种剂量的 IIc 能大幅降低小鼠的血糖水平，从 252.2 mg/dL 降至 173.8 mg/dL。IIc 令人信服的体外抗癌功效及其对正常细胞的安全性突出表明，有必要对这种前景广阔的化合物进行进一步的体内评估。这项研究凸显了苯并二恶茂衍生物作为未来开发合成抗糖尿病药物候选物的潜力。
• NAGARAJAN, K.;TALWALKER, P. K.;KULKARNI, C. L.;SHAH, R. K.;SHENOY, S. J.;+, INDIAN J. CHEM., 1985, 24, N 1, 83-97
  作者：NAGARAJAN, K.、TALWALKER, P. K.、KULKARNI, C. L.、SHAH, R. K.、SHENOY, S. J.、+

  DOI：——

  日期：——
• NEURODEGENERATIVE DISEASE THERAPEUTIC AGENT
  申请人：Ariga Hiroyoshi

  公开号：US20130109714A1

  公开（公告）日：2013-05-02

  Provided is an unprecedented composition that is not a conventional symptomatic treatment, but makes possible the fundamental treatment of current neurodegenerative diseases by inhibiting oxidative-stress induced nerve-cell death. The disclosed neurodegenerative disease therapeutic agent includes a compound, or a salt of said compound, that inhibits oxidative-stress induced nerve-cell death to a high degree and is an agent used in the treatment of neurodegenerative diseases such as Parkinson's disease.
• Nagarajan, K.; Talwalker, P. K.; Kulkarni, C. L., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 83 - 97
  作者：Nagarajan, K.、Talwalker, P. K.、Kulkarni, C. L.、Shah, R. K.、Shenoy, S. J.、Prabhu, S. S.

  DOI：——

  日期：——