1-(2-hydroxyethyl)-2-pyrrolcarboxaldehyde | 37814-49-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-hydroxyethyl)-2-pyrrolcarboxaldehyde
• 英文别名: 1-(2-Hydroxyethyl)pyrrole-2-carbaldehyde
• CAS: 37814-49-6
• 化学式: C₇H₉NO₂
• 分子量: 139.154
• InChiKey: XKVPBQSDUFXTOD-UHFFFAOYSA-N

物化性质

• 沸点：
  293.6±20.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyethyl)-2-pyrrolcarboxaldehyde 在 咪唑 、 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 三苯基膦 作用下， 以 二氯甲烷 、 苯 为溶剂， 100.0 ℃ 、8.11 MPa 条件下， 生成 1-oxo-2,3-dihydro-1H-pyrrolizidine-5-carboxaldehyde
  参考文献：
  名称：

  A tandem carbonylation/cyclization radical process of 1-(2-iodoethyl)indoles and pyrrole

  摘要：

  The AIBN-induced radical reaction of 1-(2-iodoethyl)indoles and pyrroles with Bu3SnH under 80 atm of CO was examined. Carbon monoxide was efficiently trapped by an alkyl radical to form an acyl radical which underwent intramolecular addition to the aromatic system to produce bicyclic aromatic ketones after in situ oxidation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01346-5
• 作为产物：
  描述：

  1-[2-(acetyloxy)ethyl]-1H-pyrrole-2-carboxaldehyde 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成 1-(2-hydroxyethyl)-2-pyrrolcarboxaldehyde
  参考文献：
  名称：

  Benzothiazinone and benzoxazinone compounds

  摘要：

  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。

  公开号：

  US07049312B1

文献信息

• Synthesis and Cytotoxic Activity of 2,6-Diarylidenecyclohexanones and their 6-Amino-1,3-dimethyluracil Monoadducts
  作者：Erika Madeleyne Ramos-Rivera、Cuauhtemoc Alvarado、Jose D. Solano、Luis Roa de la Fuente、Angeles Dominguez-Rivera、Miguel Angel Vilchis-Reyes、Miguel Angel Martinez-Urbina

  DOI：10.2174/1570180815666180105164032

  日期：2018.8.27

  Purpose: The aim of this study was to synthesize a series of symmetrical 2,6- diarylidenecyclohexanones (1-6) and their 6-amino-1,3-dimethyluracil monoadducts (7-10) to evaluate their cytotoxicity in a panel of cell lines. Secondly, to evaluate the effect of the most potent compound on the cell cycle of HeLa cells. Methods: The 2,6-diarylidenecyclohexanones (1-6) were synthesized by the Claisen-Schmidt condensation using cyclohexanone and the corresponding aromatic aldehyde. Monoadducts (7-10) were obtained relying in a one-pot procedure, involving a 1,4-addition of 6-amino-1,3-dimethyluracil followed by self-condensation. The cytotoxicity assay was performed using the MTT assay. The IC50 value was obtained from the dose-response curve at 48 h of treatment. HeLa cell cycle analysis was performed by flow cytometry using propidium iodide to quantify the DNA content. Results: Four of the synthesized 2,6-diarylidenecyclohexanones displayed moderate cytotoxicity in HeLa, K562, MCF7, SW480 and C33 human cell lines ranging from 15.5 to 63.2 µM. Compound 5 was the most potent in K562 (IC50 15.5 µM), C-33 (IC50 16.6 µM) and HeLa (19.0 µM) cell lines. In contrast, when a 6-amino-1,3-dimethyluracil group was added to the 2,6-diarylidenecyclohexanones, the activity was lost. In addition, we showed that compound 5 produces disruption in the cell cycle of HeLa cells, producing an increment in both the sub-G0/G1 and the G0/G1 phase population with a concomitant decrease in the S phase. Conclusion: Compound 1-3 and 5, which are 2,6-diarylidenecyclohexanone derivatives, are cytotoxic on human cell lines. The formation of monoadducts of 6-amine-1,3-dimethyluracil (7-10) was detrimental for the cytotoxic potency. The appearance of a Sub G0/G1 cell population peak, on HeLa cells treated with compound 5, suggests this compound possibly induces an apoptotic cell death.

  目的：本研究旨在合成一系列对称的 2,6-二芳基亚癸环己酮（1-6）及其 6-氨基-1,3-二甲基尿嘧啶单加成物（7-10），以评估它们在一系列细胞系中的细胞毒性。其次，评估最有效化合物对 HeLa 细胞周期的影响。 方法：2,6-二亚芳基环己酮（1-6）是利用环己酮和相应的芳香醛通过克莱森-施密特缩合反应合成的。单加成物（7-10）是通过一锅程序获得的，涉及 6-氨基-1,3-二甲基尿嘧啶的 1,4 加成，然后进行自缩合。细胞毒性试验采用 MTT 法进行。根据处理 48 小时后的剂量-反应曲线得出 IC50 值。通过流式细胞仪对 HeLa 细胞周期进行分析，使用碘化丙啶对 DNA 含量进行定量。 结果：合成的四种 2,6-二亚芳基环己酮在 HeLa、K562、MCF7、SW480 和 C33 人体细胞系中显示出中等程度的细胞毒性，范围在 15.5 至 63.2 µM 之间。化合物 5 对 K562（IC50 15.5 µM）、C-33（IC50 16.6 µM）和 HeLa（19.0 µM）细胞株的作用最强。相反，当在 2,6-二亚二萜环己酮中加入 6-氨基-1,3-二甲基尿嘧啶基团时，活性就会丧失。此外，我们还发现化合物 5 会扰乱 HeLa 细胞的细胞周期，导致亚 G0/G1 期和 G0/G1 期细胞数量增加，同时 S 期细胞数量减少。 结论：化合物 1-3 和 5 是 2,6-二亚芳基环己酮衍生物，对人类细胞株具有细胞毒性。6-胺-1,3-二甲基尿嘧啶（7-10）形成的单加成物对细胞毒性效力不利。用化合物 5 处理的 HeLa 细胞出现了 Sub G0/G1 细胞群峰值，这表明该化合物可能会诱导细胞凋亡。
• BENZOTHIAZINONE AND BENZOXAZINONE COMPOUNDS
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP1181282A2

  公开（公告）日：2002-02-27
• US7049312B1
  申请人：——

  公开号：US7049312B1

  公开（公告）日：2006-05-23
• [EN] BENZOTHIAZINONE AND BENZOXAZINONE COMPOUNDS<br/>[FR] COMPOSES DE BENZOTHIAZINONE ET DE BENZOXAZINONE
  申请人：BASF AG

  公开号：WO2000075139A2

  公开（公告）日：2000-12-14

  Q is - N=or CR2; X is S, O or NOR3; Y is-O-, -S-, -SO- or -SO¿2?-; R and R?1¿ 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.