5-chloro-3-hydroxy-3-(2'-oxopropyl)indolin-2-one | 76325-67-2

• 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: 5-chloro-3-hydroxy-3-(2'-oxopropyl)indolin-2-one
• 英文别名: 5-chloro-3-hydroxy-3-(2-oxopropyl)indolin-2-one；5-chloro-3-(2-oxopropyl)-3-hydroxy-2-oxindole；5-chloro-3-hydroxy-3-(2-oxopropyl)-1H-indol-2-one
• CAS: 76325-67-2
• 化学式: C₁₁H₁₀ClNO₃
• mdl: MFCD07545638
• 分子量: 239.658
• InChiKey: ZSAGYDHNYJBYTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-3-hydroxy-3-(2'-oxopropyl)indolin-2-one 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 生成 (E)-5-chloro-3-(2-oxopropylidene)indolin-2-one
  参考文献：
  名称：

  Acylideneoxoindoles: A new class of reversible inhibitors of human transglutaminase 2

  摘要：

  Inhibitors of human transglutaminase 2 (TG2) are anticipated to be useful in the therapy of a variety of diseases including celiac sprue as well as certain CNS disorders and cancers. A class of 3-acylidene-2-oxoindoles was identified as potent reversible inhibitors of human TG2. Structure-activity relationship analysis of a lead compound led to the generation of several potent, competitive inhibitors. Analogs with significant non-competitive character were also identified, suggesting that the compounds bind at one or more allosteric regulatory sites on this multidomain enzyme. The most active compounds had K(i) values below 1.0 mu M in two different kinetic assays for human TG2, and may therefore be suitable for investigations into the role of TG2 in physiology and disease in animals. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.037
• 作为产物：
  描述：

  5-氯靛红 、 丙酮 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79 %的产率得到5-chloro-3-hydroxy-3-(2'-oxopropyl)indolin-2-one
  参考文献：
  名称：

  3-fluoro-3-substituted oxindoles 抗癌靶标的设计、合成和计算机研究

  摘要：

  靛红和取代的靛红经过与各种酮的羟醛缩合。将所得的 3-羟基化合物转化为氟衍生物。由此获得的 3-fluoro-3-substituted oxindoles 被筛选用于针对抗癌靶标 VEGFR2 和 GSK-3β 的 Insilco 评估。该研究表明，氟化合物在其活性位点显示出结合。特别是，化合物4i、4n和4q显示出最好的结合亲和力和与它们各自的共结晶配体相似的疏水相互作用。

  DOI：

  10.1016/j.jfluchem.2023.110134

文献信息

• Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1
  作者：Saurav Paul、Ashalata Roy、Suman Jyoti Deka、Subhankar Panda、Gopal Narayan Srivastava、Vishal Trivedi、Debasis Manna

  DOI：10.1039/c7md00226b

  日期：——

  oxindoles from L-Trp, tryptamine and isatin. Compounds with C3-substituted oxindole moieties showed moderate inhibitory activity against the purified human IDO1 enzyme. Their optimization led to the identification of potent compounds, 6, 22, 23 and 25 (IC50 = 0.19 to 0.62 μM), which are competitive inhibitors of IDO1 with respect to L-Trp. These potent compounds also showed IDO1 inhibition potencies in

  吲哚胺2,3-二加氧酶1（IDO1）被认为是治疗癌症，慢性感染和其他与免疫抑制有关的疾病的重要治疗靶标。在理解IDO1酶的催化机理方面的最新进展表明，L-色氨酸（L- Trp ）向N-甲酰基kynurenine的转化通过环氧化物中间态进行。因此，我们从L -Trp，色胺和靛红合成了一系列3-取代的羟吲哚。具有C3取代的羟吲哚基团的化合物对纯化的人IDO1酶表现出中等的抑制活性。他们的优化导致了鉴定有效的化合物的，6，22，23和25（IC 50 = 0.19至0.62μM），它们是IDO1相对于L -Trp的竞争性抑制剂。这些有效的化合物还在MDA-MB-231细胞中的低微摩尔范围（IC 50 = 0.33–0.49μM）中显示出IDO1抑制能力。这些有效化合物在不同模型的癌细胞（MDA-MB-231，A549和HeLa）和巨噬细胞（J774A.1）中的细胞毒性微不足道。对于这些化合物，还
• Synthesis of potential anticonvulsants: Condensation of isatins with acetone and related ketones
  作者：F.D. Popp、R. Parson、B.E. Donigan

  DOI：10.1002/jps.2600691035

  日期：1980.10

  Substituted isatins were condensed with acetone and other ketones to give analogs of 3-hydroxy-3-acetonyloxindole. Some of these alcohols were dehydrated. Several compounds with anticonvulsant activity were obtained.

  将取代的靛红与丙酮和其他酮缩合，得到3-羟基-3-丙酮酰新吲哚的类似物。这些醇中有些是脱水的。获得了几种具有抗惊厥活性的化合物。
• Synthesis of functionalized 2-oxindoles by Friedel–Crafts reactions
  作者：Makafui Gasonoo、Douglas A. Klumpp

  DOI：10.1016/j.tetlet.2015.06.028

  日期：2015.8

  The product aryl-substituted 2-oxindoles are formed in generally good yields. With substituted arenes such as toluene, bromobenzene, or anisole, the Friedel–Crafts reactions occur with excellent regioselectivity. A mechanism is proposed involving carbocationic electrophiles leading to the aromatic substitution chemistry.

  已经制备了一系列丙酮基取代的3-羟基-2-氧吲哚，并与芳烃在超酸促进的Friedel-Crafts反应中反应。产物芳基取代的2-氧吲哚通常以良好的产率形成。对于取代的芳烃，例如甲苯，溴苯或苯甲醚，Friedel-Crafts反应的区域选择性极好。提出了涉及碳阳离子亲电试剂导致芳族取代化学的机理。
• Ordered short channel mesoporous silica modified with 1,3,5-triazine–piperazine as a versatile recyclable basic catalyst for cross-aldol, Knoevenagel and conjugate addition reactions with isatins
  作者：Naveen Gupta、Tamal Roy、Debashis Ghosh、Sayed H. R. Abdi、Rukhsana I. Kureshy、Noor-ul H. Khan、Hari C. Bajaj

  DOI：10.1039/c5ra00406c

  日期：——

  A recyclable triazine–piperazine immobilized silica supported material was explored as a heterogeneous catalyst for indole skeletal synthesized from isatins at RT.

  一种可回收的三嗪-哌嗪固定在硅胶支撑材料上的材料被探索作为在室温下从异吲哚酮合成的杂环骨架的非均相催化剂。
• Glucose-containing imidazolium salt-catalyzed cross-aldol reaction of isatins and unactivated ketones
  作者：Yu Wan、Rui Yuan、Hao Cui、Xiao-xiao Zhang、Ming-qi Li、Jiang-biao Xu、Peng-fei Dou、Long-yan Zhang、Hui Wu

  DOI：10.1007/s11164-017-3246-3

  日期：2018.4

  Ketone–ketone cross-aldol reaction of isatins and unactivated ketones was catalyzed by glucose-containing imidazolium salt β-1-imidazole-2,3,4,6-tetra- o -hydroxy- d -glucopyranosyl bromide in neutral condition to generate 3-alkyl-3-hydroxyindolin-2-ones in excellent yield.

  含葡萄糖的咪唑鎓盐β-1-咪唑-2,3,4,6-四氢呋喃-丁酮催化靛红与未活化酮的酮-酮交叉羟醛反应。 Ø -羟基- d -葡糖吡喃糖基溴在中性条件下生成3-烷基-3-羟基吲哚-2-酮的产率很高。