1-(oxiran-2-ylmethyl)-1H-indole-3-carbaldehyde | 312973-20-9

• 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-(oxiran-2-ylmethyl)-1H-indole-3-carbaldehyde
• 英文别名: 1-(oxiran-2-ylmethyl)indole-3-carbaldehyde
• CAS: 312973-20-9
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: CWPXSZCBFXTZHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  90-92 °C(Solv: benzene (71-43-2))
• 沸点：
  395.3±12.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(oxiran-2-ylmethyl)-1H-indole-3-carbaldehyde 在 三乙胺 作用下， 以 苯 为溶剂， 反应 0.67h， 生成 N-[1-(4-methypiperazin-1-ylcarbonyl)-2-(1-(oxiran-2-ylmethyl)-1H-indol-3-yl)vinyl]benzamide
  参考文献：
  名称：

  1-（环氧乙烷-2-基甲基）-1 H-吲哚-3-甲醛的合成及其与活性亚甲基化合物的反应

  摘要：

  用表氯醇处理吲哚-3-甲醛，得到1-（环氧乙烷-2-基甲基）-1H-吲哚-3-甲醛，使其与1，3-二甲基巴比妥酸或丙二腈反应，得到丁烯缩合产物，保留了产物。环氧乙烷环。与芳酰基甘氨酸的反应产物的结构取决于条件。在乙酸酐中，同时发生恶唑酮环的形成和环氧乙烷片段的双酰化作用。在三乙胺存在下使用氯甲酸乙酯只能进行杂环化过程。当用环胺（N-甲基哌嗪或吗啉）处理时，在产物中恶唑酮环的开环会形成相应的酰胺。

  DOI：

  10.1007/s10593-011-0878-x
• 作为产物：
  描述：

  吲哚 在 potassium carbonate 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 29.0h， 生成 1-(oxiran-2-ylmethyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  2-羟丙基连接的吲哚唑类衍生物作为潜在的多功能抗菌候选物，可有效抑制 MRSA 的活性并响应炎症因子

  摘要：

  开发了一类新的 2-羟丙基连接的吲哚唑类衍生物作为潜在的抗菌剂。特别是，化合物4a显示出显着的抑制 MRSA 的能力（MIC = 6 μM），并且还能够对炎症因子作出反应。

  DOI：

  10.1002/asia.202300054

文献信息

• Benzothiazinone and benzoxazinone compounds
  申请人：Abbott GmbH & Co. KG

  公开号：US07049312B1

  公开（公告）日：2006-05-23

  Q is —N=or CR2 X is S, O or NOR3 Y is —O—, —S—, —SO— or —SO2— R and R1 are each, independently, H, a substituted or unsubstituted aliphatic, aromatic, heteroaromatic or aralkyl group R2 is H or a substituent R3 is H, or —C(O)R4 R4 is a substituted or unsubstituted aliphatic or aromatic group n is an integer from 0 to 1 Chemical compounds having structural formula I and physiologically acceptable salts thereof, are inhibitors of serine/threonine and tyrosine kinase activity. Several of the tyrosine kinases, whose activity is inhibited by these chemical compounds, are involved in angiogenic processes. Thus, these chemical compounds can ameliorate disease states where angiogenesis or endothelial cell hyperproliferation is a factor. These compounds can be used to treat cancer and hyperproliferative disorders.

  Q是-N=或CR2 X是S，O或NOR3 Y是-O-，-S-，-SO-或-SO2-R和R1分别是H，一个取代或未取代的脂肪族，芳香族，杂环芳香族或芳基烃基团R2是H或一个取代基R3是H，或-C(O)R4 R4是一个取代或未取代的脂肪族或芳香族团n是从0到1的整数具有结构式I和其生理上可接受的盐的化合物，是丝氨酸/苏氨酸激酶和酪氨酸激酶活性的抑制剂。这些化合物抑制的几种酪氨酸激酶参与血管生成过程。因此，这些化合物可以改善血管生成或内皮细胞过度增殖是因素的疾病状态。这些化合物可用于治疗癌症和过度增殖性疾病。
• Rational modification of the lead molecule: Enhancement in the anticancer and dihydrofolate reductase inhibitory activity
  作者：Jagroop Kaur、Sukhmeet Kaur、Palwinder Singh

  DOI：10.1016/j.bmcl.2016.03.015

  日期：2016.4

  By using molecular docking studies, the practice of fragment based drug discovery is conceptualized by introducing oxindole and iso-propanol moieties in our previous lead molecule 1. The resulting compound 2 exhibited competitive inhibition and favorable Ka and Ki for hDHFR. The screening of compound 2 at 60 cell line panel of human tumor cell lines showed its considerably better efficacy than compound

  通过使用分子对接研究，通过在我们之前的先导分子1中引入羟吲哚和异丙醇部分，对基于片段的药物发现的实践进行了概念化。将得到的化合物2表现出竞争性抑制和有利ķ一个和ķ我为hDHFR。在人肿瘤细胞系的60个细胞系中对化合物2的筛选显示出其比化合物1更好的功效，因此将2的候选资格作为据点有待进一步研究。
• Charge transport materials having a nitrogen-containing-heterocycle hydrazone group
  申请人：Lygaitis Ramunas

  公开号：US20060177750A1

  公开（公告）日：2006-08-10

  Improved organophotoreceptor comprises an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising: (a) a charge transport material having the formula: where E comprises a functional group selected from the group consisting of a reactive ring group, an ethylenically unsaturated group, a hydrazone group, and an azine group; R 1 , R 2 , and R 3 comprise, each independently, H or an organic group; X is a bond or a linking group, with the proviso that when E comprises a reactive ring group, X is a linking group; and Y is a nitrogen-containing aromatic heterocyclic group; and (b) a charge generating compound.

  改进的有机光感受器包括一个电导基底和位于电导基底上的光电导元件，该光电导元件包括：(a) 具有以下化学式的电荷传输材料：其中 E 包括从反应性环基团、乙烯不饱和基团、腙基团和偶氮基团中选择的官能团；R1、R2 和 R3 分别独立地表示 H 或有机基团；X 是键或连接基团，但当 E 包括反应性环基团时，X 是连接基团；Y 是含氮芳香杂环基团；以及 (b) 一个电荷生成化合物。
• Mechanism Inspired Development of Rationally Designed Dihydrofolate Reductase Inhibitors as Anticancer Agents
  作者：Palwinder Singh、Matinder Kaur、Shaveta Sachdeva

  DOI：10.1021/jm300644g

  日期：2012.7.26

  On the basis of structural analysis of dihydrofolate reductase (DHFR) (cocrystallized separately with NADPH, dihydrofolate and NADPH, trimethoprim), compounds 2 and 3 were optimized for inhibition of DHFR. Appreciable tumor growth inhibitory activities of compounds 2 and 3 over 60 human tumor cell lines were recorded. Combination of syringaldehyde and indole moieties in these two compounds was rationalized

  根据二氢叶酸还原酶（DHFR）（与NADPH，二氢叶酸和NADPH，甲氧苄氨嘧啶分别共结晶）的结构分析，优化了化合物2和3对DHFR的抑制作用。记录了化合物2和3在60种人类肿瘤细胞系中的明显的肿瘤生长抑制活性。丁香醛和这两种化合物在吲哚部分的组合是由化合物的合成合理化4 - 7，10，和11，其被发现具有比化合物更少的肿瘤生长抑制活性2和3。此外，UV-vis和NMR光谱研究表明化合物2和3与DHFR有显着的相互作用，并且在这些化合物的存在下观察到其催化活性受到抑制。因此，修饰甲氧苄氨嘧啶是一种没有肿瘤生长抑制作用的抗菌药物，导致化合物2和3的开发具有明显的抗癌活性，这似乎是由于DHFR的抑制。
• Triblock Conjugates: Identification of a Highly Potent Antiinflammatory Agent
  作者：Palwinder Singh、Jagroop Kaur、Gurjit Singh、Rajbir Bhatti

  DOI：10.1021/acs.jmedchem.5b00952

  日期：2015.8.13

  Rationally designed conjugates of chrysin, indole, and barbituric acid were synthesized and screened for their antiinflammatory activities through in vitro and in vivo experiments. Improved over the previously reported chrysin indole pyrazole conjugates and also in comparison to the chrysin, indole, and barbituric acid based COX-2 inhibitors, the new compounds have displayed significantly better IC50 for COX-2 and some of them also exhibited inhibition of 5-LOX enzyme. For one of the test compounds, IC50 for COX-2 and 5-LOX was 1 and 1.5 nM, respectively. Investigations of Swiss Albino mice through capsaicin induced paw lickings and dextran induced inflammation showed that these compounds possess appreciable analgesic and antiinflammatory activities. K-i, K-a, and Delta G for the enzyme compound interaction were calculated and found to be in agreement with The experimental results were supported by the molecular docking studies of the compounds in the active site of COX-2 and 5-LOX. Overall, a highly promising antiinflammatory agent was identified. the biological data.