2-(hydroxymethyl)-1-methyl-5-(methylsulfonyl)pyrrole | 335606-58-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(hydroxymethyl)-1-methyl-5-(methylsulfonyl)pyrrole
• 英文别名: (1-Methyl-5-(methylsulfonyl)-1h-pyrrol-2-yl)methanol；(1-methyl-5-methylsulfonylpyrrol-2-yl)methanol
• CAS: 335606-58-1
• 化学式: C₇H₁₁NO₃S
• 分子量: 189.235
• InChiKey: TXBURTJOUFPRGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-1-methyl-5-(methylsulfonyl)pyrrole 在 溴 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.25h， 生成 (6-{5-[bis(tert-butoxycarbonyl)amino]}-1-(chloromethyl)-1,2-dihydro-3H-benzo[e]indol-3-yl-6-oxo-1-hexyl)-N,N-dimethyl-N-{[1-methyl-5-(methylsulfonyl)-pyrrol-2-yl]methyl}ammonium bromide
  参考文献：
  名称：

  Weight loss effects of quaternary salts of 5-amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indoles; structure–activity relationships

  摘要：

  Quaternary salt analogues based on the DNA minor groove binder and adenine N3 alkylating agent 5-amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole (aminoCBI) show remarkable effects on the body weight of mice (a long-term failure to gain weight relative to matched controls with no loss of appetite or perceptible deterioration in health) following administration of a single (non-toxic) dose between about 0.5-5 mu mol/kg. The nature of the quaternizing group was not important, but a related hydroxyCBI analogue was much less effective. Compounds where the chloro group was replaced by a hydrogen or hydroxy group (thus abrogating DNA alkylating capability) showed no weight control activity. It is speculated, based on other studies, that the marked long-term weight control effect is due to inhibition of bile flow into the intestine and reduced absorption of triglycerides, together with accelerated cell death in spleen and white adipose tissues due to drug accumulation there. This class of compound may serve as interesting tools for further study of these phenomena. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.007
• 作为产物：
  描述：

  5-Methanesulfonyl-1-methyl-1H-pyrrole-2-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以68%的产率得到2-(hydroxymethyl)-1-methyl-5-(methylsulfonyl)pyrrole
  参考文献：
  名称：

  用于二阶非线性光学的新型磺酰基取代的吡咯发色团的合成

  摘要：

  磺酰基取代吡咯发色团的第一合成1 - 4和它们的UV-VIS吸收，二阶非线性光学性质和热稳定性进行说明，并与那些在苯，噻吩和呋喃类似物5 - 9。

  DOI：

  10.1016/s0040-4039(00)02232-2

文献信息

• [EN] NITROGEN RING CONTAINING COMPOUNDS FOR TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] COMPOSÉS CONTENANT UN CYCLE AZOTÉ POUR LE TRAITEMENT DE TROUBLES INFLAMMATOIRES
  申请人：WEINGARTEN M DAVID

  公开号：WO2012135669A1

  公开（公告）日：2012-10-04

  The invention provides compounds, pharmaceutical compositions and methods of treatment of inflammatory disorders including a compound of Formula I, or its pharmaceutically acceptable salt, ester, pharmaceutically acceptable derivative or prodrug wherein R1, R2, R3, R4, X, Y, W, Z and Q are as defined herein.

  这项发明提供了化合物、药物组合物和治疗炎症性疾病的方法，包括式I的化合物，或其药用可接受的盐、酯、药用可接受的衍生物或前药，其中R1、R2、R3、R4、X、Y、W、Z和Q如本文所定义。
• Synthesis of novel sulfonyl-substituted pyrrole chromophores for second-order nonlinear optics
  作者：Shang-Shing P Chou、Yu-Hsin Yeh

  DOI：10.1016/s0040-4039(00)02232-2

  日期：2001.2

  The first synthesis of sulfonyl-substituted pyrrole chromophores 1–4 and their UV–vis absorptions, second-order nonlinear optical properties and thermal stability are described and compared with those of the benzene, thiophene and furan analogues 5–9.

  磺酰基取代吡咯发色团的第一合成1 - 4和它们的UV-VIS吸收，二阶非线性光学性质和热稳定性进行说明，并与那些在苯，噻吩和呋喃类似物5 - 9。
• Weight loss effects of quaternary salts of 5-amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indoles; structure–activity relationships
  作者：Moana Tercel、Ralph J. Stevenson、Guo-Liang Lu、Stephen M. Stribbling、William R. Wilson、Michele A. Tatnell、Rebecca N. Marnane、Kathleen G. Mountjoy、William A. Denny

  DOI：10.1016/j.bmc.2011.12.007

  日期：2012.1

  Quaternary salt analogues based on the DNA minor groove binder and adenine N3 alkylating agent 5-amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole (aminoCBI) show remarkable effects on the body weight of mice (a long-term failure to gain weight relative to matched controls with no loss of appetite or perceptible deterioration in health) following administration of a single (non-toxic) dose between about 0.5-5 mu mol/kg. The nature of the quaternizing group was not important, but a related hydroxyCBI analogue was much less effective. Compounds where the chloro group was replaced by a hydrogen or hydroxy group (thus abrogating DNA alkylating capability) showed no weight control activity. It is speculated, based on other studies, that the marked long-term weight control effect is due to inhibition of bile flow into the intestine and reduced absorption of triglycerides, together with accelerated cell death in spleen and white adipose tissues due to drug accumulation there. This class of compound may serve as interesting tools for further study of these phenomena. (C) 2011 Elsevier Ltd. All rights reserved.