1-(p-methoxy-phenethyl)-isatin | 1198772-93-8

• 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-(p-methoxy-phenethyl)-isatin
• 英文别名: 1-(p-methoxypenethyl)isatin；1-[2-(4-Methoxyphenyl)ethyl]indole-2,3-dione
• CAS: 1198772-93-8
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: GTJUANGTCQFMIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-吲哚酮 、 1-(p-methoxy-phenethyl)-isatin 在 盐酸 作用下， 以 水 、 溶剂黄146 为溶剂， 200.0 ℃ 、400.01 kPa 条件下， 反应 0.5h， 以34%的产率得到1-(p-methoxy-phenethyl)-isoindigo
  参考文献：
  名称：

  Synthesis and evaluation of functionalized isoindigos as antiproliferative agents

  摘要：

  A series of functionalized isoindigos structurally related to meisoindigo (1-methylisoindigo), a therapeutic agent used for the treatment of a form of leukemia, were synthesized and evaluated for antiproliferative activities on a panel of human cancer cells. Two promising compounds (1-phenpropylisoindigo and 1-(p-methoxy-phenethyl)-isoindigo) that were more potent than meisoindigo and comparable to 6-bromoindirubin-3'-oxime on leukemic K562 and liver HuH7 cells were identified. Structure-activity relationships showed the importance of keeping one of the lactam NH in an unsubstituted state. Substitution of the other lactam NH with aryl or arylalkyl side chains retained or improved activity in most instances. An intact exocyclic double bond was also essential, possibly to maintain planarity and rigidity of the iso-indigo scaffold. None of the compounds were found to inhibit CDK2 in an in vitro assay, in spite of reports linking the antiproliferative activities of meisoindigo and other isoindigos to CDK2 inhibition. Hence, these functionalized isoindigos disrupted cell growth and proliferation by other mechanistic pathways that did not involve CDK2 inhibition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.008
• 作为产物：
  描述：

  1-(2-溴乙基)-1H-吲哚-2,3-二酮 、 4-甲氧基苯硼酸 在 sodium tetrachloropalladate(II) 、 potassium carbonate 、 tris(4,6-dimethyl-3-sulfonatophenyl)phosphine trisodium salt hydrate 作用下， 以 水 为溶剂， 以29%的产率得到1-(p-methoxy-phenethyl)-isatin
  参考文献：
  名称：

  伯烷基卤化物与芳基硼类的完全水相且空气相容的交叉偶联：一种可能且简便的方法

  摘要：

  水相转化具有许多优点，包括减少环境影响和增加生物分子调节的机会。尽管已经进行了几项研究以实现芳基卤化物在水性条件下的交叉偶联，但迄今为止，催化工具箱中缺少在水性条件下伯烷基卤化物交叉偶联的方法，并且被认为是不可能的。水中的卤代烷偶联遇到严重的问题。其原因包括β-氢化物消除的强烈倾向、对空气和水高度敏感的催化剂和试剂的需要，以及许多亲水基团对交叉偶联条件的不耐受。在这里，我们报告了一种广泛适用且易于使用的方法，通过使用简单且市售的实验室稳定试剂来交叉偶联水和空气中的水溶性卤代烷。三磺化芳基膦 TXPTS 与水溶性钯盐 Na 2 PdCl 4结合，可在温和、完全水性的条件下实现水溶性卤代烷与芳基硼酸、硼酸酯和氟硼酸盐的 Suzuki-Miyaura 偶联。多种具有挑战性的功能，包括未受保护的氨基酸、肽内的非天然卤代氨基酸以及除草剂，可以在水中多样化。结构复杂的天然产物被用作试验台，展示海洋天然

  DOI：

  10.1021/acscatal.3c00252

文献信息

• Exploring the Anticancer Activity of Functionalized Isoindigos: Synthesis, Drug-like Potential, Mode of Action and Effect on Tumor-Induced Xenografts
  作者：Xi Kai Wee、Tianming Yang、Mei Lin Go

  DOI：10.1002/cmdc.201200018

  日期：2012.5

  have focused on developing analogues with more desirable physicochemical profiles. Here, we investigated the structure–activity relationship (SAR) of meisoindigo with respect to its antiproliferative activity on leukemic K562 cells and found that appending a phenalkyl side chain onto the lactam NH resulted in analogues that retained good activity. Furthermore, analogues in which the phenyl ring was

  Meisoindigo一直用作靛红素的替代品，用于治疗慢性粒细胞白血病（CML）已有数年之久。鉴于其较差的溶解度和不稳定的吸收，一些研究集中在开发具有更理想的理化特性的类似物。在这里，我们研究了美isoindigo对白血病K562细胞的抗增殖活性的结构-活性关系（SAR），发现将苯烷基侧链附加在内酰胺NH上可产生保留良好活性的类似物。此外，苯环被碱性杂环取代的类似物在保持可接受的抗增殖特性的同时，其溶解性明显高于meisoindigo。最有前途的类似物（E）-1-（2-（4-甲基哌嗪-1-基）乙基）-[3,3'-联吲哚基亚基] -2,2'-二酮（5-4）在整个恶性细胞中比meisoindigo更有效，其溶解度至少是meisoindigo的40倍，几乎没有或没有在溶液中聚集的趋势，并且能够显着延长使用K562诱导的异种移植物的动物的寿命。从机制上讲，它诱导凋亡细胞死亡并破坏K562细胞从G 1到G
• Synthesis and evaluation of functionalized isoindigos as antiproliferative agents
  作者：Xi Kai Wee、Wee Kiang Yeo、Bing Zhang、Vincent B.C. Tan、Kian Meng Lim、Tong Earn Tay、Mei-Lin Go

  DOI：10.1016/j.bmc.2009.09.008

  日期：2009.11

  A series of functionalized isoindigos structurally related to meisoindigo (1-methylisoindigo), a therapeutic agent used for the treatment of a form of leukemia, were synthesized and evaluated for antiproliferative activities on a panel of human cancer cells. Two promising compounds (1-phenpropylisoindigo and 1-(p-methoxy-phenethyl)-isoindigo) that were more potent than meisoindigo and comparable to 6-bromoindirubin-3'-oxime on leukemic K562 and liver HuH7 cells were identified. Structure-activity relationships showed the importance of keeping one of the lactam NH in an unsubstituted state. Substitution of the other lactam NH with aryl or arylalkyl side chains retained or improved activity in most instances. An intact exocyclic double bond was also essential, possibly to maintain planarity and rigidity of the iso-indigo scaffold. None of the compounds were found to inhibit CDK2 in an in vitro assay, in spite of reports linking the antiproliferative activities of meisoindigo and other isoindigos to CDK2 inhibition. Hence, these functionalized isoindigos disrupted cell growth and proliferation by other mechanistic pathways that did not involve CDK2 inhibition. (C) 2009 Elsevier Ltd. All rights reserved.
• Fully Aqueous and Air-Compatible Cross-Coupling of Primary Alkyl Halides with Aryl Boronic Species: A Possible and Facile Method
  作者：Samuel Molyneux、Rebecca J. M. Goss

  DOI：10.1021/acscatal.3c00252

  日期：2023.5.5

  air by using simple and commercially available bench-stable reagents. The trisulfonated aryl phosphine TXPTS in combination with a water-soluble palladium salt Na2PdCl4 allowed for the Suzuki–Miyaura coupling of water-soluble alkyl halides with aryl boronic acids, boronic esters, and borofluorate salts in mild, fully aqueous conditions. Multiple challenging functionalities, including unprotected amino

  水相转化具有许多优点，包括减少环境影响和增加生物分子调节的机会。尽管已经进行了几项研究以实现芳基卤化物在水性条件下的交叉偶联，但迄今为止，催化工具箱中缺少在水性条件下伯烷基卤化物交叉偶联的方法，并且被认为是不可能的。水中的卤代烷偶联遇到严重的问题。其原因包括β-氢化物消除的强烈倾向、对空气和水高度敏感的催化剂和试剂的需要，以及许多亲水基团对交叉偶联条件的不耐受。在这里，我们报告了一种广泛适用且易于使用的方法，通过使用简单且市售的实验室稳定试剂来交叉偶联水和空气中的水溶性卤代烷。三磺化芳基膦 TXPTS 与水溶性钯盐 Na 2 PdCl 4结合，可在温和、完全水性的条件下实现水溶性卤代烷与芳基硼酸、硼酸酯和氟硼酸盐的 Suzuki-Miyaura 偶联。多种具有挑战性的功能，包括未受保护的氨基酸、肽内的非天然卤代氨基酸以及除草剂，可以在水中多样化。结构复杂的天然产物被用作试验台，展示海洋天然