5-chloro-N-((2S,3R)-3-(3,5-difluorophenyl)-4,4,4-trifluoro-1-hydroxybutan-2-yl)thiophene-2-sulfonamide | 1104028-84-3

• 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: 5-chloro-N-((2S,3R)-3-(3,5-difluorophenyl)-4,4,4-trifluoro-1-hydroxybutan-2-yl)thiophene-2-sulfonamide
• 英文别名: 5-chlorothiophene-2-sulfonic acid [(1S,2R)-2-(3,5-difluorophenyl)-3,3,3-trifluoro-1-hydroxymethylpropyl]amide；5-chloro-thiophene-2-sulfonic acid [(1S,2R)-2-(3,5-difluoro-phenyl)-3,3,3-trifluoro-1-hydroxymethyl-propyl]-amide；5-chloro-N-[(1S,2R)-2-(3,5-difluorophenyl)-3,3,3-trifluoro-1-(hydroxymethyl)propyl]thiophene-2-sulfonamide；5-chloro-N-[(2S,3R)-3-(3,5-difluorophenyl)-4,4,4-trifluoro-1-hydroxybutan-2-yl]thiophene-2-sulfonamide
• CAS: 1104028-84-3
• 化学式: C₁₄H₁₁ClF₅NO₃S₂
• 分子量: 435.823
• InChiKey: XTQMGWVYLPUFGO-ZWNOBZJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-chloro-N-((2S,3R)-3-(3,5-difluorophenyl)-4,4,4-trifluoro-1-hydroxybutan-2-yl)thiophene-2-sulfonamide 、 、 N-三氟乙酰基吗啉 、 1-溴-3,5-二氟苯 以to form 1-(3,5-difluoro-phenyl)-2,2,2-trifluoro-ethanone的产率得到1-(3,5-二氟苯基)-2,2,2-三氟乙酮
  参考文献：
  名称：

  PROCESS FOR THE PREPARATION OF TRIFLUOROALKYL-PHENYL AND HETEROCYCLIC SULFONAMIDES

  摘要：

  介绍了一种新的三氟乙酰化试剂，即N-三氟乙酰基吗啉。该试剂在制备苯基和杂环磺酰胺化合物方面非常有用。因此，使用N-三氟乙酰基吗啉描述了以下结构的磺酰胺化合物的制备方法，其中R1和R2在此处定义。可以按照本文所述的方法制备的磺酰胺化合物包括使用N-三氟乙酰基吗啉制备的5-氯噻吩-2-磺酸[(1S,2R)-2-(3,5-二氟苯基)-3,3,3-三氟-1-羟甲基丙基]-酰胺。

  公开号：

  US20090023903A1
• 作为产物：
  描述：

  N-((2S,3R)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-(3,5-difluorophenyl)-4,4,4-trifluoro-1-oxobutan-2-yl)-5-chlorothiophene-2-sulfonamide 在 锂硼氢 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 以76%的产率得到5-chloro-N-((2S,3R)-3-(3,5-difluorophenyl)-4,4,4-trifluoro-1-hydroxybutan-2-yl)thiophene-2-sulfonamide
  参考文献：
  名称：

  PROCESSES AND INTERMEDIATES FOR THE PREPARATION OF HETEROCYCLIC SULFONAMIDE COMPOUNDS

  摘要：

  描述了制备式(I)化合物的方法，其中R1-R3在此处定义，以及制备其中间体的方法。还描述了选择性对映体制备具有以下结构的手性化合物的方法，其中R2和R3在此处定义。

  公开号：

  US20090023930A1

文献信息

• INHIBITORS OF BETA AMYLOID PRODUCTION
  申请人：Caggiano Thomas J.

  公开号：US20090023801A1

  公开（公告）日：2009-01-22

  Novel sulfonamide compounds useful in the treatment of conditions related to the production of beta-amyloid are described, as are routes to their preparation. The sulfonamide compounds are of the following structure, wherein R 1 -R 3 are defined herein. Also provided are pharmaceutical compositions containing these compounds and/or prodrugs of these compounds and a physiologically compatible carrier. These compounds are specifically useful for inhibiting beta amyloid production, and treating Alzheimer's Disease, amyloid angiopathy, cerebral amyloid angiopathy, systemic amyloidosis, hereditary cerebral hemorrhage with amyloidosis of the Dutch type, inclusion body myositis, mild cognitive impairment (MCI) and Down's syndrome.

  描述了在与β-淀粉样蛋白产生相关的疾病治疗中有用的新型磺胺化合物，以及它们的制备途径。这些磺胺化合物具有以下结构，其中R1-R3在此定义。还提供了含有这些化合物和/或这些化合物的前药以及与生理兼容载体的药物组合物。这些化合物特别适用于抑制β淀粉样蛋白的产生，并治疗阿尔茨海默病、淀粉样血管病、脑淀粉样血管病、全身淀粉样病、荷兰型遗传性脑出血伴有淀粉样蛋白沉积、包涵体肌炎、轻度认知障碍（MCI）和唐氏综合征。
• Practical Enantioselective Synthesis of a 3-Aryl-3-trifluoromethyl-2-aminopropanol Derivative
  作者：Asaf Alimardanov、Antonia Nikitenko、Terrence J. Connolly、Gregg Feigelson、Anita W. Chan、Zhixian Ding、Mousumi Ghosh、Xinxu Shi、Jianxin Ren、Eric Hansen、Roger Farr、Michael MacEwan、Sam Tadayon、Dane M. Springer、Anthony F. Kreft、Douglas M. Ho、John R. Potoski

  DOI：10.1021/op900216v

  日期：2009.11.20

  Development of a large-scale enantioselective synthesis of a lead compound containing a 3-aryl-3-trifluoromethyl-2-aminopropanol core is described. A single isomer of 3,3-disubstituted acrylic acid derivative was prepared via Perkin condensation or Horner−Wadsworth−Emmons olefination, followed by hydrolysis. The acid was converted to a chiral acryloxazolidinone derivative. Hydrogenation of the latter

  描述了开发大规模对映选择性合成包含3-芳基-3-三氟甲基-2-氨基丙醇核的铅化合物的方法。通过珀金缩合或霍纳-沃兹沃思-埃蒙斯烯化反应制备3,3-二取代丙烯酸衍生物的单一异构体，然后进行水解。将该酸转化为手性丙烯恶唑烷酮衍生物。后者在MgBr 2存在下在Pd / C上的氢化反应是通过螯合控制的构象进行的，以高选择性产生所需的异构体。随后的Evans叠氮化，氢化，手性助剂的还原裂解和磺酰化以高总收率提供了作为单一异构体的目标化合物。
• COMPOSITIONS CONTAINING O-SULFATE AND O-PHOSPHATE CONTAINING ARYL SULFONAMIDE DERIVATIVES USEFUL AS beta-AMYLOID INHIBITORS
  申请人：LI David Zenan

  公开号：US20090181932A1

  公开（公告）日：2009-07-16

  A synthetic compound characterized by having the structure of formula I or II or a pharmaceutically acceptable salt and/or hydrate thereof is provided. Formula I and formula II are defined as follows. wherein R 1 is substituted aryl or substituted heteroaryl; R 2 and R 3 are independently selected from the group consisting of CF 3 , substituted phenyl, C 1 -C 4 alkyl, substituted C 1 -C 4 alkyl, (CF 3 ) n C 1 -C 4 alkyl, (CF 3 ) n (substituted C 1 -C 4 alkyl), provided that when R 2 or R 3 is CF 3 , the other is not an unsubstituted alkyl; R 4 and R 4′ are independently selected from the group consisting of M, C 1 -C 4 alkyl, phenyl, and benzyl, wherein M is a metal ion is selected from the group consisting of sodium, lithium, calcium, magnesium and potassium, or R 4 and R 4′ are taken together to form a cyclic structure. Methods of making such compounds and uses thereof are also provided.

  提供一种具有I或II式结构或其药学上可接受的盐和/或水合物的合成化合物。其中，公式I和公式II定义如下：其中R1为取代芳基或取代杂环芳基；R2和R3分别选自CF3、取代苯基、C1-C4烷基、取代C1-C4烷基、(CF3)nC1-C4烷基、(CF3)n(取代C1-C4烷基)的群，但当R2或R3为CF3时，另一个不是未取代的烷基；R4和R4′分别选自M、C1-C4烷基、苯基和苄基的群，其中M是选择自钠、锂、钙、镁和钾的金属离子，或R4和R4′结合形成环状结构。还提供制备这种化合物的方法和其用途。
• [EN] PROCESSES AND INTERMEDIATES FOR THE PREPARATION OF HETEROCYCLIC SULFONAMIDE COMPOUNDS<br/>[FR] PROCÉDÉS ET INTERMÉDIAIRES POUR LA PRÉPARATION DE COMPOSÉS SULFONAMIDE HÉTÉROCYCLIQUES
  申请人：WYETH CORP

  公开号：WO2009012203A1

  公开（公告）日：2009-01-22

  Methods for preparing compound of Formula (I) are described, wherein R1-R3 are defined herein, as are methods for preparing the intermediates formed therein. Formula (I) Also described are methods for enantioselectively preparing a chiral compound of the following structure, wherein R2 and R3 are defined herein. Formula (II).

  本文描述了制备式(I)化合物的方法，其中R1-R3如本文所定义，并描述了制备其中间体的方法。式(I)。还描述了对具有以下结构的手性化合物进行对映选择性制备的方法，其中R2和R3如本文所定义。式(II)。
• [EN] INHIBITORS OF BETA AMYLOID PRODUCTION<br/>[FR] INHIBITEURS DE PRODUCTION DE BÊTA AMYLOÏDE
  申请人：WYETH CORP

  公开号：WO2009012205A1

  公开（公告）日：2009-01-22

  Novel sulfonamide compounds useful in the treatment of conditions related to the production of beta-amyloid are described, as are routes to their preparation. The sulfonamide compounds are of the following structure, wherein R4-R3 are defined herein. Also provided are pharmaceutical compositions containing these compounds and/or prodrugs of these compounds and a physiologically compatible carrier. These compounds are specifically useful for inhibiting beta amyloid production, and treating Alzheimer's Disease, amyloid angiopathy, cerebral amyloid angiopathy, systemic amyloidosis, hereditary cerebral hemorrhage with amyloidosis of the Dutch type, inclusion body myositis, mild cognitive impairment (MCI) and Down's syndrome.