5-Methoxyninhydrin | 188179-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-Methoxyninhydrin
• 英文别名: 5-Methoxyindene-1,2,3-trione
• CAS: 188179-82-0
• 化学式: C₁₀H₆O₄
• 分子量: 190.155
• InChiKey: JEENPBOSAIFXCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Methoxyninhydrin 在 水 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 2,2-二羟基-5-甲氧基茚-1,3-二酮
  参考文献：
  名称：

  Bowden, Keith; Rumpal, Sanjay, Journal of Chemical Research, Miniprint, 1997, # 2, p. 355 - 374

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-二羟基-5-甲氧基茚-1,3-二酮 以 氯苯 为溶剂， 生成 5-Methoxyninhydrin
  参考文献：
  名称：

  Bowden, Keith; Rumpal, Sanjay, Journal of Chemical Research, Miniprint, 1997, # 2, p. 355 - 374

  摘要：

  DOI：

文献信息

• INDANONE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALTS OR OPTICAL ISOMERS THEREOF, PREPARATION METHOD FOR SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING VIRAL DISEASES
  申请人：Jung Young Sik

  公开号：US20140114068A1

  公开（公告）日：2014-04-24

  Disclosed are novel indanone derivatives, pharmaceutically acceptable salts thereof or enantiomers, a preparation method thereof, and a pharmaceutical composition for the prevention or treatment of viral diseases, comprising the same as an active ingredient. The indanone derivatives have excellent inhibitory activity against picornaviruses including coxsackie-, entero-, echo-, Polio-, and rhinoviruses, as well as exhibiting low cytotoxicity, so that they can be useful as an active ingredient of a pharmaceutical composition for the prevention or treatment of viral diseases including poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, hand-foot-and-mouth disease, vesicular disease, hepatitis A, myositis, myocarditis, pancreatitis, diabetes, epidemic myalgia, encephalitis, flu, herpangina, foot-and-mouth disease, asthma, chronic obstructive pulmonary disease, pneumonia, sinusitis or otitis media.

  揭示了新颖的茚酮衍生物，其药用盐或对映体，以及其制备方法和作为活性成分的用于预防或治疗病毒性疾病的药物组合物。这些茚酮衍生物对包括柯萨奇病毒、肠道病毒、回声病毒、脊髓灰质炎病毒和鼻病毒在内的小RNA病毒具有出色的抑制活性，并且具有低细胞毒性，因此它们可用作预防或治疗包括小儿麻痹症、瘫痪、急性出血性结膜炎、病毒性脑膜炎、手足口病、水疱病、甲型肝炎、肌炎、心肌炎、胰腺炎、糖尿病、流行性肌痛、脑炎、流感、手足口病、哮喘、慢性阻塞性肺病、肺炎、鼻窦炎或中耳炎等病毒性疾病的药物组合物的活性成分。
• Photochemical Behavior of Indane-1,2,3-trione in Degassed Alcoholic Solutions: Formation of 3-Substituted Phthalides
  作者：Jiro Tatsugi、Tomoaki Hara、Yasuji Izawa

  DOI：10.1246/cl.1997.177

  日期：1997.2

  the major product together with 3-alkoxyphthalides. 3-Alkoxycarbonylphthalides may be derived from the reaction between alcohols and the spirooxiranone intermediate, generated photochemically by cleavage of the bond between two carbonyl groups of indane-1,2,3-trione via a cyclobutenone biradical derivative.

  在脱气的醇溶液中辐照茚满-1,2,3-三酮可得到 3-烷氧基羰基苯酞和 3-烷氧基苯酞作为主要产物。3-烷氧基羰基邻苯二甲醚可以衍生自醇和螺环酮中间体之间的反应，通过环丁烯酮双自由基衍生物裂解茚满-1,2,3-三酮的两个羰基之间的键以光化学方式产生。
• Design, synthesis, and characterization of oxadiazolopyrazine analogs with application as anticancer agents
  作者：Wei‐Chia Chen、Chia‐Ling Chen、Tzu‐Ting Chang、Feng‐Chun Hsieh、Wei‐Sheng Chen、Wen‐Shan Li

  DOI：10.1002/jccs.202100438

  日期：2022.2

  Here, we describe the synthesis and evaluation of a class of cell-permeable indeno-oxadiazolopyrazine analogs as the anticancer agents. A new and facile approach to the synthesis of substituted analogs of indeno-oxadiazolopyrazine is illustrated. We find that the designed indeno-oxadiazolopyrazines, 3, 4, 10, 11, 15, and 16, act as potent anticancer agents compared to camptothecin, topoisomerase I

  在这里，我们描述了一类可渗透细胞的茚并恶二唑并吡嗪类似物作为抗癌剂的合成和评价。说明了合成茚并恶二唑并吡嗪的取代类似物的一种新的简便方法。我们发现设计的茚并恶二唑并吡嗪3、4、10、11、15和16，与拓扑异构酶 I 抑制剂喜树碱相比，可作为有效的抗癌剂。这些观察结果表明，在 A 环的 C-5、C-6 和 C-8 位置上的给电子基团（甲氧基）或在 C-6 和 C-7 位置上的吸电子基团（氟）对 MDA-MB-231、BT549 和 MCF7 细胞系的抗增殖活性需要茚并恶二唑并吡嗪。
• Decarbonylative cycloaddition of 1<i>H</i>-indene-1,2,3-trione and norbornene <i>via</i> rhodium(<scp>i</scp>)-catalyzed carbon–carbon bond cleavage
  作者：Zhenzhu Hu、Yuhang Wang、Peng Ma、Jianhui Wang、Guiyan Liu

  DOI：10.1039/d2nj01708c

  日期：——

  2,3-Dihydro-1H-inden-1-one derivatives were synthesized by a [5+2−2] decarbonylative cycloaddition of 1H-indene-1,2,3-trione and norbornene via rhodium(I) catalyzed direct carbon–carbon bond cleavage. A catalytic system combining [Rh(COD)Cl]2 (5.0 mol%) and rac-BINAP(10 mol%) ligand was optimal for these transformations. Various functional groups were tolerated under standard reaction conditions. Although

  2,3-Dihydro-1 H -inden-1-one 衍生物是由 1 H -indene-1,2,3-trione 和降冰片烯通过铑( I ) 直接催化的 [5+2−2] 脱羰环加成反应合成的碳-碳键断裂。结合 [Rh(COD)Cl] 2 (5.0 mol%) 和rac -BINAP(10 mol%) 配体的催化体系是这些转化的最佳选择。在标准反应条件下可以耐受各种官能团。尽管在大多数情况下反应没有显示出区域选择性，但一些在 4 位具有-OMe、-CN 或强吸电子-CF 3基团的底物显示出高区域选择性。
• DABCO-based ionic liquid-promoted synthesis of indeno-benzofurans derivatives: Investigation of antioxidant and antidiabetic activities
  作者：Narges Alipour Saqa、Shiva Khalil-Moghaddam、Ashraf Sadat Shahvelayati

  DOI：10.1515/hc-2022-0153

  日期：2022.12.8

  A simple and effective method for synthesis of indeno-benzofurans derivatives using polyphenols and ninhydrins is explored using an acidic catalyst based on DABCO (1,4-diaza bicycle [2.2.2] octane)-based ionic liquid. The products of these types of reactions have very low yields without catalysts, but with DABCO-AIL, the yields are excellent, reaction times are reduced, and the media are cleaner. Using infrared (IR), proton nuclear magnetic resonance (¹H NMR), Carbon-13 nuclear magnetic resonance (¹³C NMR), and mass spectrometry, the structures of products can be confirmed. There is evidence that oxidative stress plays a role in the pathophysiology of numerous diseases, including diabetes. Therapeutic antioxidants are promising candidates for the prevention and treatment of such diseases. To investigate the antioxidant properties of all synthesized derivatives, the 2,2-diphenyl-1-picrylhydrazylhydrazyl-hydrate (DPPH) assay was used. Derivatives 3d and 4 with the highest antioxidant effect (with IC₅₀ value of 0.015 µmol/mL) were selected to evaluate the anti-diabetic effect using the Bernfeld method. The best result was seen at 0.8 mg/mL of 4 derivative and results of the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) test revealed that 4 at this concentration lacked cellular toxicity, too.

  摘要 利用基于 DABCO（1,4-二氮杂双环[2.2.2]辛烷）离子液体的酸性催化剂，探索了一种利用多酚和茚并呋喃衍生物合成茚并呋喃衍生物的简单而有效的方法。在没有催化剂的情况下，这类反应的产物收率很低，但使用 DABCO-AIL 后，收率极高，反应时间缩短，介质也更清洁。利用红外线（IR）、质子核磁共振（1H NMR）、碳-13 核磁共振（13C NMR）和质谱分析，可以确认产物的结构。有证据表明，氧化应激在包括糖尿病在内的多种疾病的病理生理学中发挥作用。治疗性抗氧化剂是预防和治疗此类疾病的有效候选物质。为了研究所有合成衍生物的抗氧化特性，采用了 2,2-二苯基-1-苦基肼水合物（DPPH）测定法。我们选择了抗氧化效果最好（IC50 值为 0.015 µmol/mL）的衍生物 3d 和 4，用 Bernfeld 法评估其抗糖尿病效果。4 号衍生物在 0.8 毫克/毫升时效果最佳，3-(4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四氮唑（MTT）试验结果表明，4 号衍生物在此浓度下也没有细胞毒性。