N-(4-hydroxymethylphenyl)benzenesulfonamide | 90312-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-hydroxymethylphenyl)benzenesulfonamide
• 英文别名: N-(4-Hydroxymethyl-phenyl)-benzenesulfonamide；N-[4-(hydroxymethyl)phenyl]benzenesulfonamide
• CAS: 90312-03-1
• 化学式: C₁₃H₁₃NO₃S
• mdl: MFCD12913576
• 分子量: 263.317
• InChiKey: NJYQEVYFSKGUAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxymethylphenyl)benzenesulfonamide 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 1-(phenylsulfonyl)benzo[1,2:2',3']thieno[5',4'-b]carbazole
  参考文献：
  名称：

  Pyrazolopyridines, their preparation and their medical use

  摘要：

  该发明涉及按照一般式I及其盐制备的吡唑吡啶类化合物，包括含有该吡唑吡啶类化合物的药物组合物，以及制备该吡唑吡啶类化合物的方法，以及将其用于制造用于治疗血管生长失调疾病或伴随血管生长失调的疾病的药物组合物的用途，其中这些化合物有效干扰血管生成素，从而影响Tie2信号传导。

  公开号：

  EP1683796A1
• 作为产物：
  描述：

  4-(苯磺酰基氨基)苯甲酸乙酯 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 生成 N-(4-hydroxymethylphenyl)benzenesulfonamide
  参考文献：
  名称：

  Stereoselectivity in the Wittig Reaction of Aromatic Ketones: Origin of Preference for the Olefin Geometry

  摘要：

  Investigation of the stereoselectivity observed in the Wittig reaction of aromatic ketones with ''nonstabilized'' phosphonium ylides revealed that the nature of the substituent on the phenyl ring of phenyl S-pyridyl ketone determined the stereoselectivity. Generally the Wittig reaction of such ketones with carboxy phosphonium ylides proceeded preferentially to yield (Z)-olefin, albeit with modest selectivity. However, the reaction with aryl sulfonamido-substituted aromatic ketones resulted in high (E)-stereoselectivity. In order to understand the origin of this high (E)-selectivity, a semiempirical conformational analysis of the four uncharged diastereomeric oxaphosphetane intermediates was performed with a cumulatively modified sampling procedure to generate initial conformations, followed by full energy optimization. Computational studies of the unsubstituted and 4-nitrophenyl-substituted oxaphosphetane intermediates were consistent with the low (Z)stereoselectivity observed. The results in the calculations of the aryl sulfonamido-substituted intermediate likewise were consistent with the high (E)-stereoselectivity observed. Calculations of the potassium-coordinated acid anion of the latter species were also performed. All calculations supported interaction of the sulfonamido and carboxylate groups by either hydrogen bonding or salt bridge formation which appears to effect the final stereochemical outcome. Furthermore, we investigated the stereoselectivity of Wittig reactions in which the sulfonamido NH or the carboxylate were removed. In both cases, the (Z)-olefin was formed preferentially, thereby supporting the existence of intramolecular hydrogen bonding or salt bridge formation.

  DOI：

  10.1021/jo00106a029

文献信息

• Pyrazolopyridines, their preparation and their medical use
  申请人：Schering Aktiengesellschaft

  公开号：EP1683796A1

  公开（公告）日：2006-07-26

  The invention relates to pyrazolopyridines according to the general Formula I and the salts thereof, to pharmaceutical compositions comprising the pyrazolopyridines and to a method of preparing the pyrazolopyrimidines as well as the use thereof for manufacturing a pharmaceutical composition for the treatment of diseases of dysregulated vascular growth or of diseases which are accompanied with dysregulated vascular growth, wherein the compounds effectively interfere with angiopoietin and therefore influence Tie2 signalling.

  该发明涉及按照一般式I及其盐制备的吡唑吡啶类化合物，包括含有该吡唑吡啶类化合物的药物组合物，以及制备该吡唑吡啶类化合物的方法，以及将其用于制造用于治疗血管生长失调疾病或伴随血管生长失调的疾病的药物组合物的用途，其中这些化合物有效干扰血管生成素，从而影响Tie2信号传导。
• Pyrazolopyridines and salts thereof, a pharmaceutical composition comprising said compounds, a method of preparing same and use of same
  申请人：Schwede Wolfgang

  公开号：US20060252754A1

  公开（公告）日：2006-11-09

  The invention relates to pyrazolopyridines according to the general formula (I): and salts thereof, to pharmaceutical compositions comprising said pyrazolopyridines and to a method of preparing said pyrazolopyridines as well as the use thereof for manufacturing a pharmaceutical composition for the treatment of diseases of dysregulated vascular growth or of diseases which are accompanied with dysregulated vascular growth, wherein the compounds effectively interfere with angiopoietin and therefore influence Tie2 signalling.

  该发明涉及通式（I）的吡唑吡啶及其盐，包括含有该吡唑吡啶的制药组合物以及制备该吡唑吡啶的方法，以及将其用于制造用于治疗异常血管生长疾病或伴随异常血管生长的疾病的药物组合物的用途，其中该化合物有效地干扰血管生成素并因此影响Tie2信号传导。
• Stereoselectivity in the Wittig Reaction of Aromatic Ketones: Origin of Preference for the Olefin Geometry
  作者：Kumiko Takeuchi、Jonathan W. Paschal、Richard J. Loncharich

  DOI：10.1021/jo00106a029

  日期：1995.1

  Investigation of the stereoselectivity observed in the Wittig reaction of aromatic ketones with ''nonstabilized'' phosphonium ylides revealed that the nature of the substituent on the phenyl ring of phenyl S-pyridyl ketone determined the stereoselectivity. Generally the Wittig reaction of such ketones with carboxy phosphonium ylides proceeded preferentially to yield (Z)-olefin, albeit with modest selectivity. However, the reaction with aryl sulfonamido-substituted aromatic ketones resulted in high (E)-stereoselectivity. In order to understand the origin of this high (E)-selectivity, a semiempirical conformational analysis of the four uncharged diastereomeric oxaphosphetane intermediates was performed with a cumulatively modified sampling procedure to generate initial conformations, followed by full energy optimization. Computational studies of the unsubstituted and 4-nitrophenyl-substituted oxaphosphetane intermediates were consistent with the low (Z)stereoselectivity observed. The results in the calculations of the aryl sulfonamido-substituted intermediate likewise were consistent with the high (E)-stereoselectivity observed. Calculations of the potassium-coordinated acid anion of the latter species were also performed. All calculations supported interaction of the sulfonamido and carboxylate groups by either hydrogen bonding or salt bridge formation which appears to effect the final stereochemical outcome. Furthermore, we investigated the stereoselectivity of Wittig reactions in which the sulfonamido NH or the carboxylate were removed. In both cases, the (Z)-olefin was formed preferentially, thereby supporting the existence of intramolecular hydrogen bonding or salt bridge formation.
• Crystal structure of the PXR–T1317 complex provides a scaffold to examine the potential for receptor antagonism
  作者：Yu Xue、Esther Chao、William J. Zuercher、Timothy M. Willson、Jon L. Collins、Matthew R. Redinbo

  DOI：10.1016/j.bmc.2006.12.026

  日期：2007.3

  The human pregnane X receptor (PXR) recognizes a range of structurally and chemically distinct ligands and plays a key role in regulating the expression of protective gene products involved in the metabolism and excretion of potentially harmful compounds. The identification and development of PXR antagonists is desirable as a potential way to control the up-regulation of drug metabolism pathways during the therapeutic treatment of disease. We present the 2.8 angstrom resolution crystal structure of the PXR ligand binding domain (LBD) in complex with T0901317 (T 1317), which is also an agonist of another member of the orphan class of the nuclear receptor superfamily, the liver X receptor (LXR). In spite of differences in the size and shape of the receptors' ligand binding pockets, key interactions with this ligand are conserved between human PXR and human LXR. Based on the PXR-T1317 structure, analogues of T 1317 were generated with the goal of designing an PXR antagonist effective via the receptor's ligand binding pocket. We find that selectivity in activating PXR versus LXR was achieved; such compounds may be useful in addressing neurodegenerative diseases like Niemann-Pick C. We were not successful, however, in producing a PXR antagonist. Based on these observations, we conclude that the generation of PXR antagonists targeted to the ligand binding pocket may be difficult due to the promiscuity and structural conformability of this xenobiotic sensor. (c) 2006 Elsevier Ltd. All rights reserved.
• UREA DERIVATIVES AND THEIR USE AS ACAT-INHIBITORS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0784612A1

  公开（公告）日：1997-07-23