(Z)-2-(4'-methoxybenzylidene)-1,2-dihydroindol-3-one | 38114-44-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (Z)-2-(4'-methoxybenzylidene)-1,2-dihydroindol-3-one
• 英文别名: (Z)-2-(4-methoxybenzylidene)indolin-3-one；2-(4-Methoxyphenyl)-methylidenindolin-3-on；(2Z)-2-(4-methoxybenzylidene)-1,2-dihydro-3H-indol-3-one；(2Z)-2-[(4-methoxyphenyl)methylidene]-1H-indol-3-one
• CAS: 38114-44-2
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: LYMXAPZBYOLSEP-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-(4'-methoxybenzylidene)-1,2-dihydroindol-3-one 在 溶剂黄146 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (2E)-2-[amino-(4-methoxyphenyl)methylidene]-1H-indol-3-one
  参考文献：
  名称：

  New method for the introduction of nitro and amino groups into the arylmethylene substituent of 1-R-2-arylmethylene-3-indolinones

  摘要：

  DOI：

  10.1007/bf00767016
• 作为产物：
  描述：

  2-(4-methoxybenzylidene)indolin-3-one 以 水 为溶剂， 生成 (Z)-2-(4'-methoxybenzylidene)-1,2-dihydroindol-3-one
  参考文献：
  名称：

  Design, synthesis and investigation of water-soluble hemi-indigo photoswitches for bioapplications

  摘要：

  合成了一系列半靛衍生物，并研究了它们在水介质中的光开关性能。在水中表现出最佳光致变色性能的二甲氧基半靛衍生物被确定为有望用于开发生物分子的光开关结合剂的平台。开发了向二甲氧基半靛核心引入烷基氨基侧链的合成方法，从而获得了具有光开关荧光性能的RNA结合半靛衍生物。

  DOI：

  10.3762/bjoc.15.275

文献信息

• In quest of small-molecules as potent non-competitive inhibitors against influenza
  作者：Khushboo Malbari、Priyanka Saha、Mamta Chawla-Sarkar、Shanta Dutta、Swita Rai、Mamata Joshi、Meena Kanyalkar

  DOI：10.1016/j.bioorg.2021.105139

  日期：2021.9

  neuraminidase, unlike sialic acid and oseltamivir in molecular docking studies. All molecules reduced the viral titer and exhibited non-cytotoxicity along with cryo-protective property towards MDCK cells. Molecules (Z)-2-(3′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2f), (Z)-2-(4′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2g) and 2-(2′-Methoxy-phenyl)-1H-quinolin-4-one (3a) were the most interesting

  一系列支架，即 aurones、3-indolinones、4-quinolones 和肉桂酸-哌嗪杂化物，被设计、合成并在体外针对 A/H1N1pdm09 病毒进行了研究。与分子对接研究中的唾液酸和奥司他韦不同，设计的分子采用不同的结合方式，即在神经氨酸酶的430-cavity中。所有分子都降低了病毒滴度并表现出非细胞毒性以及对 MDCK 细胞的冷冻保护特性。分子 ( Z )-2-(3'-Chloro-benzylidene)-1,2-dihydro-indol-3-one ( 2f ), ( Z )-2-(4'-Chloro-benzylidene)-1,2- dihydro-indol-3-one ( 2g ) 和 2-(2'-Methoxy-phenyl)-1H-quinolin-4-one ( 3a) 是本研究中鉴定出的最有趣的分子，与参考竞争性和非竞争性抑制剂相比，奥司他韦 (EC
• Fused Bis(hemi‐indigo): Broad‐Range Wavelength‐Independent Photoswitches
  作者：Daria V. Berdnikova、Bernhard M. Kriesche、Thomas Paululat、Thomas S. Hofer

  DOI：10.1002/chem.202202752

  日期：2022.12.20

  Bis(hemi-indigo) derivatives are introduced as unique photoswitches with wavelength-independent isomeric ratios in photostationary states. The wavelength-independent photoswitching, high bistability and significant overlap between the photoswitch absorption and the solar spectrum make bis(hemi-indigo) derivatives interesting candidates for MOST applications.

  双（半靛蓝）衍生物作为独特的光开关引入，在光静止状态下具有与波长无关的异构比。与波长无关的光开关、高双稳态以及光开关吸收与太阳光谱之间的显着重叠使得双（半靛蓝）衍生物成为 MOST 应用的有趣候选者。
• Nucleophile-Controlled Trapping of Gold Carbene by Nitriles and Water: Synthesis of 5<i>H</i>-Pyrimido[5,4-<i>b</i>]indoles and 2-Benzylidene-3-indolinones
  作者：Yun-Long Zhu、Yi-Fan Dong、Si-Ru Wang、You-Gui Li、Xiang Wu、Long-Wu Ye

  DOI：10.1021/acs.orglett.3c03856

  日期：2024.1.26

  A gold-catalyzed, nucleophile-controlled cascade reaction of N-(2-azidophenyl-ynyl)methanesulfonamides with nitriles and water is described that provides structurally diverse 5H-pyrimido[5,4-b]indoles and 2-benzylidene-3-indolinones in good to excellent yields. Mechanistic studies indicate that the β-sulfonamido-α-imino gold carbene is the key intermediate which is generated through the gold-catalyzed

  描述了N- (2-叠氮苯基-炔基)甲磺酰胺与腈和水的金催化亲核试剂控制级联反应，提供结构多样的 5 H-嘧啶基[5,4 -b ]吲哚和 2-亚苄基-3-二氢吲哚酮的收率良好至极好。机理研究表明，β-磺酰胺基-α-亚氨基金卡宾是金催化N- (2-叠氮苯基-炔基)甲磺酰胺环化生成的关键中间体，并与腈进行正式的[4 + 2]级联成环反应分别与水发生分子内S N 2′型反应。
• Novel Pyridazino[4,3-<i>b</i>]indoles with Dual Inhibitory Activity against <i>Mycobacterium </i><i>t</i><i>uberculosis</i> and Monoamine Oxidase
  作者：Valeriya S. Velezheva、Patrick J. Brennan、Vladimir Yu. Marshakov、Dmitrij V. Gusev、Inessa N. Lisichkina、Alexander S. Peregudov、Larisa N. Tchernousova、Tatiana G. Smirnova、Sofia N. Andreevskaya、Alexei E. Medvedev

  DOI：10.1021/jm030479g

  日期：2004.6.1

  Tuberculosis is one of the most common infectious diseases known to man. About 37% of the world's population (about 1.86 billion people) are infected with Mycobacterium tuberculosis. According to the World Health Organization, every year approximately 8 million people develop active tuberculosis and almost 2 million of those die from the disease. The incidence of multidrug-resistant tuberculosis (MDR-TB) is increasing. The present drug regimen for treating tuberculosis has been in existence for 30 years. New drugs that will shorten total treatment duration, improve the treatment of MDR-TB, and address latent tuberculosis are the most urgent need of tuberculosis control programs. A new series of synthetic 3-amino-4-arylpyridazino[4,3-b]indoles (pyridazinoindoles) were identified as inhibitors of Mycobacterium tuberculosis. The design, synthesis, and antimycobacterial activity of these compounds are described. While the most active compounds are still not comparable to the front-line drugs rifampicin and isoniazid, they do show promise. Most of the pyridazinoindoles with appreciable antituberculosis activity also inhibit monoamine oxidase, suggestive of a novel inhibitory effect on mycobacterial redox reactions.
• VELEZHEVA, V. S.;NEVSKIJ, K. V.;SUVOROV, N. N., XIMIYA GETEROTSIKL. SOEDIN., 1985, N 2, 246-247
  作者：VELEZHEVA, V. S.、NEVSKIJ, K. V.、SUVOROV, N. N.

  DOI：——

  日期：——