3-hydroxymethyl-1H-pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-hydroxymethyl-1H-pyrrole
• 英文别名: indole-3-carbinol；1H-Pyrrole-3-methanol；1H-pyrrol-3-ylmethanol
• 化学式: C₅H₇NO
• 分子量: 97.1167
• InChiKey: KQBJJBPSKBSJTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-hydroxymethyl-1H-pyrrole 在 manganese(IV) oxide 作用下， 以 甲醇 为溶剂， 生成 吡咯-3-甲醛
  参考文献：
  名称：

  Identification of N-acylhydrazone derivatives as novel lactate dehydrogenase A inhibitors

  摘要：

  Glycolysis is drastically increased in tumors and it is the main route to energy production with a minor use of oxidative phosphorylation. Among the key enzymes in the glycolytic process, LDH is emerging as one of the most interesting targets for the development of new inhibitors. In this context, in the present work, we carried out a virtual screening procedure followed by chemical modifications of the identified structures according to a "hit-to-lead" process. The effects of the new molecules were preliminary probed against purified human LDH-A. The compounds active at low micromolar level were additionally characterized for their activity on some cellular metabolic processes by using Raji human cell line. Within the series, 1 was considered the best candidate, and a more detailed characterization of its biological properties was performed. In Raji cells exposed to compound 1 we evidenced the occurrence of effects usually observed in cancer cells after LDH-A inhibition: reduced lactate production and NAD/NADH ratio, apoptosis. The flow cytometry analysis of treated cells also showed cell cycle changes compatible with effects exerted at the glycolytic level. Finally, in agreement with the data obtained with other inhibitors or by silencing LDH-A expression, compound 1 was found to increase Rail cells response to some commonly used chemotherapeutic agents. Taken together, all these finding are in support of the LDH-A inhibiting activity of compound 1. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.028
• 作为产物：
  描述：

  3-吡咯羧酸 在 氯化亚砜 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 3-hydroxymethyl-1H-pyrrole
  参考文献：
  名称：

  Identification of N-acylhydrazone derivatives as novel lactate dehydrogenase A inhibitors

  摘要：

  Glycolysis is drastically increased in tumors and it is the main route to energy production with a minor use of oxidative phosphorylation. Among the key enzymes in the glycolytic process, LDH is emerging as one of the most interesting targets for the development of new inhibitors. In this context, in the present work, we carried out a virtual screening procedure followed by chemical modifications of the identified structures according to a "hit-to-lead" process. The effects of the new molecules were preliminary probed against purified human LDH-A. The compounds active at low micromolar level were additionally characterized for their activity on some cellular metabolic processes by using Raji human cell line. Within the series, 1 was considered the best candidate, and a more detailed characterization of its biological properties was performed. In Raji cells exposed to compound 1 we evidenced the occurrence of effects usually observed in cancer cells after LDH-A inhibition: reduced lactate production and NAD/NADH ratio, apoptosis. The flow cytometry analysis of treated cells also showed cell cycle changes compatible with effects exerted at the glycolytic level. Finally, in agreement with the data obtained with other inhibitors or by silencing LDH-A expression, compound 1 was found to increase Rail cells response to some commonly used chemotherapeutic agents. Taken together, all these finding are in support of the LDH-A inhibiting activity of compound 1. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.028

文献信息

• Selective Mono-reduction of Pyrrole-2,5 and 2,4-Dicarboxylates
  作者：Eiko Yasui、Jyunpei Tsuda、Satoshi Ohnuki、Shinji Nagumo

  DOI：10.1248/cpb.c16-00122

  日期：——

  Pyrrole-2,5-dicarboxylates were rapidly and selectively reduced to the corresponding mono-alcohol using 3 eq of diisobutylaluminum hydride at 0°C. Pyrrole-2,4-dicarboxylate showed the same reactivity; however, the selectivity decreased with pyrrole-3,4-dicarboxylate. When the nitrogen atom of the pyrrole-2,5-dicarboxylate is protected with a benzyl group, selective mono-reduction does not occur. Considering that furan-2,5-dicarboxylates did not give the corresponding mono-alcohol under the same conditions, the unprotected nitrogen atom of pyrrole apparently plays an important role in this selective mono-reduction.

  吡咯-2,5-二羧酸酯在0°C下使用3倍等摩尔的二异丁基铝氢化物迅速且选择性地还原为相应的单醇。吡咯-2,4-二羧酸酯显示出相同的反应性；然而，吡咯-3,4-二羧酸酯的选择性有所降低。当吡咯-2,5-二羧酸酯的氮原子被苄基保护时，选择性单还原不再发生。考虑到在相同条件下呋喃-2,5-二羧酸酯并未产生相应的单醇，显然，未保护的吡咯氮原子在此选择性单还原反应中起着重要作用。
• Pyrrolidine derivatives-CCR-3 receptor antagonists
  申请人：Syntex (U.S.A.) Inc.

  公开号：US06166015A1

  公开（公告）日：2000-12-26

  This invention relates to certain 3-aminomethylpyrrolidine derivatives of Formula (I): ##STR1## that are CCR-3 receptor antagonists, pharmaceutical compositions containing them, methods for their use and methods for preparing these compounds.

  本发明涉及某些3-氨甲基吡咯烷衍生物，其化学式为（I）：##STR1## 这些化合物是CCR-3受体拮抗剂，包括它们的制药组合物、使用方法和制备这些化合物的方法。
• A new approach to porphobilinogen and its analogs
  作者：Christine Y. de Leon、Bruce Ganem

  DOI：10.1016/s0040-4020(97)00469-9

  日期：1997.6

  The van Leusen pyrrole synthesis was used to assemble three potential precursors of porphobilinogen, one of which was converted to the natural product using a new method for the direct alkylation of beta-hydroxymethylpyrroles. (C) 1997 Elsevier Science Ltd.
• Alkylation of β-(Hydroxymethyl)pyrroles:  A New Synthesis of Porphobilinogen and Other Trisubstituted Pyrroles for Photodynamic Therapy
  作者：Christine Y. De Leon、Bruce Ganem

  DOI：10.1021/jo961987j

  日期：1996.1.1
• CN116655598
  申请人：——

  公开号：——

  公开（公告）日：——