1-Phenylcarbamoylisatin | 53460-45-0

• 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: 1-Phenylcarbamoylisatin
• 英文别名: 2,3-dioxo-N-phenylindole-1-carboxamide
• CAS: 53460-45-0
• 化学式: C₁₅H₁₀N₂O₃
• mdl: MFCD00420803
• 分子量: 266.256
• InChiKey: OYJNIYAGHTZTMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Phenylcarbamoylisatin 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 3'-Phenylspiro-2,2',5(3'H)-trione
  参考文献：
  名称：

  Quinazolin-2-ones Having a Spirohydantoin Ring. III. A General and Efficient Synthesis of 3'-Substituted Spiro(imidazolidine-4,4'(1'H)-quinazoline)-2,2',5(3'H)-triones.

  摘要：

  在三乙胺存在下，1-氨基甲酰基异沙丁鱼苷 2 与 2-乙基-2-异硫脲氢溴酸盐反应，然后在酸催化下环化生成 4-(2-乙基-2-异硫脲基)羰基-3.4-二氢-4-羟基-2(1H)-喹唑啉酮 7、4-二氢-4-羟基-2(1H)-喹唑啉酮 7 提供了一条通向 3'-取代的螺[咪唑烷-4，4'(1'H)-喹唑啉]-2，2'5(3'H)-三酮 8 的通用高产路线。

  DOI：

  10.1248/cpb.39.1694
• 作为产物：
  描述：

  2-羟基亚氨基-n-苯乙酰胺 在 硫酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-Phenylcarbamoylisatin
  参考文献：
  名称：

  Biological activities and quantitative structure-activity relationships of spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-triones as aldose reductase inhibitors

  摘要：

  A series of spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-triones were prepared and tested for aldose reductase inhibitory activity. The 6'-halogenated derivatives were found to be highly potent in vitro inhibitors of male rabbit lens aldose reductase and in vivo inhibitors of polyol accumulation in the sciatic nerves of galactosemic rats. Of these, (4R)-6'-chloro-3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione (67) showed the most potent in vitro and in vivo activities. An oral dose of 3 g/kg of compound 67 caused neither death nor behavioral abnormality in the preliminary acute toxicity study using mice and rats. Compound 67 was selected as a candidate for further evaluation. The quantitative structure-activity relationships in this series are also discussed.

  DOI：

  10.1021/jm00089a021

文献信息

• Eco-friendly chemoselective N-functionalization of isatins mediated by supported KF in 2-MeTHF
  作者：Ashenafi Damtew Mamuye、Serena Monticelli、Laura Castoldi、Wolfgang Holzer、Vittorio Pace

  DOI：10.1039/c5gc01002k

  日期：——

  A simple, versatile and eco-friendly approach to the functionalization of isatins.

  一种简单、多功能且环保的对异喹啉的官能化方法。
• Core-Structure-Motivated Design of a Phosphine-Catalyzed [3 + 2] Cycloaddition Reaction: Enantioselective Syntheses of Spirocyclopenteneoxindoles
  作者：Bin Tan、Nuno R. Candeias、Carlos F. Barbas

  DOI：10.1021/ja110147w

  日期：2011.4.6

  A novel organocatalytic asymmetric [3+2] cycloaddition reaction between methyleneindolinones and allylic compounds yielding complex spirocyclopentaneoxindoles has been developed. It provides extraordinary levels of enantioselective control involving a chiral phosphine as a nucleophilic organocatalyst. Simple precursors were used under mild conditions to construct oxindole derivatives with high enantiopurity

  已开发出一种新型有机催化不对称 [3+2] 环加成反应，在亚甲基吲哚酮和烯丙基化合物之间生成复杂的螺环戊烷氧吲哚。它提供了非凡水平的对映选择性控制，涉及手性膦作为亲核有机催化剂。在温和的条件下使用简单的前体来构建具有高对映纯度和结构多样性的羟吲哚衍生物。这种方法应该可用于这些有趣化合物的药物化学和面向多样性的合成。
• Effect of Structure of 1-Substituted Isatins on Direction of Their Reactions with Some Acetohydrazide Ammonium Derivatives
  作者：A. V. Bogdanov、A. D. Voloshina、A. S. Sapunova、N. V. Kulik、V. F. Mironov

  DOI：10.1134/s1070363220090029

  日期：2020.9

  Abstract The reaction of 1-acylisatins with Girard’s reagent T proceeds with elimination of the acyl substituent and the formation of isatin-3-hydrazone with a quaternary nitrogen atom in the side chain. Depending on the structure of the substituent in position 1, 1-(aminomethyl)isatins reacted with the Girard’s reagent T to form hydrazones either with the elimination of the aminomethyl substituent

  摘要 1-酰基赖氨酸与吉拉德试剂T的反应是消除酰基取代基，并在侧链形成带有季氮原子的isatin-3- is。取决于位置1上的取代基的结构，1-（氨基甲基）异染色质与吉拉德试剂T反应形成，同时消除了氨基甲基取代基或保留了氨基甲基取代基。在芳族片段中不具有取代基的伊斯兰衍生物对革兰氏阳性细菌金黄色葡萄球菌209p和蜡状芽孢杆菌8035表现出中等活性。显示出所获得化合物的低血液毒性。
• An Unusual Polyheterocyclic Diversity by the π-Cyclisation of <i>N</i>-Carbamoyl­iminium Ion, with or without Tandem <i>N</i>,<i>N</i>-Acetal Cleavage, from Spiro(imidazolidinoquinazolinones)
  作者：Adam Daïch、Anthony Pesquet、Servane Coste、Luc Van Hijfte

  DOI：10.1055/s-2008-1067032

  日期：2008.5

  Spiro(imidazolidinoquinazolinones), obtained easily in one step from 1-carbamoylisatins, are readily converted in three steps by successive N-alkylations and sodium borohydride regio­selective reduction into the corresponding hydroxyspirolactams. The latter are valuable platforms for further transformations via the intermediacy of N-acyliminium species and have been applied to the synthesis of original isoquinoloquinazoline, indoloquinazoline and imidazoindole derivatives.

  从 1-氨基甲酰基利萨丁一步即可轻松获得螺（咪唑烷基喹唑啉酮），通过连续的 N-烷基化和硼氢化钠区域选择性还原，可分三步轻松转化为相应的羟基吡咯内酰胺。后者是通过 N-酰亚胺中间体进行进一步转化的重要平台，已被用于合成原始的异喹唑啉、吲哚喹唑啉和咪唑吲哚衍生物。
• Facile synthetic approach towards vasorelaxant active 4-hydroxyquinazoline-4-carboxamides
  作者：Marian N. Aziz、Siva S. Panda、ElSayed M. Shalaby、Nehmedo G. Fawzy、Adel S. Girgis

  DOI：10.1039/c9ra04321g

  日期：——

  A Facile synthetic approach is reported towards 4-hydroxyquinazoline-4-carboxamides 13a–i through ring expansion of 2,3-dioxoindoline-1-carboxamides 10a–c during secondary amine 11a–d nucleophilic reaction. Single crystal X-ray studies of 10c and 13d support the structures. Some of the synthesized quinazolinecarboxamides 13 show promising vasorelaxant properties with potency higher than that of Doxazosin

  据报道，通过在仲胺11a-d亲核反应期间2,3-二氧吲哚啉-1-甲酰胺10a-c的扩环，一种简便的合成方法可用于 4-羟基喹唑啉-4-甲酰胺13a-i 。10c和13d的单晶 X 射线研究支持这些结构。通过预收缩（去甲肾上腺素盐酸盐）大鼠主动脉标准生物测定，一些合成的喹唑啉甲酰胺13显示出有希望的血管舒张特性，其效力高于多沙唑嗪。良好的分子模型（2D-QSAR，药效团）描述了生物学观察。