(R,E)-N-(6-(2-ethyl-1,3-dioxolan-2-yl)hexylidene)-2-methylpropane-2-sulfinamide | 891270-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R,E)-N-(6-(2-ethyl-1,3-dioxolan-2-yl)hexylidene)-2-methylpropane-2-sulfinamide
• 英文别名: (R)-N-[(1E)-6-(2-ethyl-1,3-dioxolan-2-yl)hexylidene]-2-methylpropane-2-sulfinamide；(NE,R)-N-[6-(2-ethyl-1,3-dioxolan-2-yl)hexylidene]-2-methylpropane-2-sulfinamide
• CAS: 891270-02-3
• 化学式: C₁₅H₂₉NO₃S
• 分子量: 303.466
• InChiKey: NYUIOYSFCVJHLE-MBNYPGIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R,E)-N-(6-(2-ethyl-1,3-dioxolan-2-yl)hexylidene)-2-methylpropane-2-sulfinamide 在 盐酸 、 硼烷四氢呋喃络合物 、 dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) 、 叔丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.5h， 生成 (S)-9-amino-9-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)nonan-3-one
  参考文献：
  名称：

  [EN] INHIBITORS OF HISTONE DEACETYLASE USEFUL FOR THE TREATMENT OR PREVENTION OF HIV INFECTION
  [FR] INHIBITEURS DE DÉSACÉTYLASE D'HISTONE UTILES POUR TRAITER OU PRÉVENIR UNE INFECTION PAR LE VIH

  摘要：

  公开号：

  WO2020096916A3
• 作为产物：
  描述：

  6-(2-ethyl-1,3-dioxolan-2-yl)-N-methoxy-N-methylhexanamide 在 titanium(IV) tetraethanolate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (R,E)-N-(6-(2-ethyl-1,3-dioxolan-2-yl)hexylidene)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Synthesis of HDAC Inhibitor Libraries via Microscale Workflow

  摘要：

  DOI：

  10.1021/acsmedchemlett.0c00596

文献信息

• [EN] INHIBITORS OF HISTONE DEACETYLASE USEFUL FOR THE TREATMENT OR PREVENTION OF HIV INFECTION<br/>[FR] INHIBITEURS D'HISTONE DÉSACÉTYLASE UTILES POUR LE TRAITEMENT OU LA PRÉVENTION D'UNE INFECTION PAR LE VIH
  申请人：MERCK SHARP & DOHME

  公开号：WO2020190827A1

  公开（公告）日：2020-09-24

  The present invention relates to Compounds of Formula I and Ia and pharmaceutically acceptable salts or prodrug thereof, wherein R1, R2, X, A and B are as defined herein. The present invention also relates to compositions comprising at least one compound of Formula I or Ia, and methods of using the compounds of Formula I or Ia for treating or preventing HIV infection in a subject.

  本发明涉及公式I和Ia的化合物以及其药用盐或前药，其中R1、R2、X、A和B如本文所定义。本发明还涉及包含至少一种公式I或Ia化合物的组合物，以及使用公式I或Ia化合物治疗或预防受试者的HIV感染的方法。
• Discovery of ethyl ketone-based HDACs 1, 2, and 3 selective inhibitors for HIV latency reactivation
  作者：Wensheng Yu、Jian Liu、Younong Yu、Vivian Zhang、Dane Clausen、Joseph Kelly、Scott Wolkenberg、Douglas Beshore、Joseph L. Duffy、Christine C. Chung、Robert W. Myers、Daniel J. Klein、James Fells、Kate Holloway、Jin Wu、Guoxin Wu、Bonnie J. Howell、Richard J.O. Barnard、Joseph Kozlowski

  DOI：10.1016/j.bmcl.2020.127197

  日期：2020.7

  A novel series of ethyl ketone based HDACs 1, 2, and 3 selective inhibitors have been identified with good enzymatic and cellular activity and high selectivity over HDACs 6 and 8. These inhibitors contain a spirobicyclic group in the amide region. Compound 13 stands out as a lead due to its good potency, high selectivity, and reasonable rat and dog PK. Compounds 33 and 34 show good potency and rat

  已经鉴定出一系列新的基于乙基酮的HDAC 1、2和3选择性抑制剂，具有良好的酶促和细胞活性，并且具有比HDAC 6和8更高的选择性。这些抑制剂在酰胺区包含一个螺双环基团。化合物13由于其良好的效能，高选择性和合理的大鼠和犬PK而脱颖而出。化合物33和34也显示出良好的效力和大鼠PK曲线。
• Discovery of Ethyl Ketone-Based Highly Selective HDACs 1, 2, 3 Inhibitors for HIV Latency Reactivation with Minimum Cellular Potency Serum Shift and Reduced hERG Activity
  作者：Wensheng Yu、Jian Liu、Dane Clausen、Younong Yu、Joseph L. Duffy、Ming Wang、Shouning Xu、Lin Deng、Takao Suzuki、Christine C. Chung、Robert W. Myers、Daniel J. Klein、James I. Fells、M. Katharine Holloway、Jin Wu、Guoxin Wu、Bonnie J. Howell、Richard J. O. Barnard、Joseph Kozlowski

  DOI：10.1021/acs.jmedchem.0c02150

  日期：2021.4.22
• A general approach to homochiral α-amino substituted bromo-heteroaromatics suitable for two-dimensional rapid analogue synthesis
  作者：Carsten Schultz-Fademrecht、Olaf Kinzel、István E. Markó、Tomas Pospisil、Silvia Pesci、Michael Rowley、Philip Jones

  DOI：10.1016/j.tet.2009.08.013

  日期：2009.11

  An efficient and general synthesis of homochiral alpha-amino substituted bromo-heteroaromatics B using a diastereoselective 1,2-addition has been developed. The obtained heteroaromatic intermediates allow for a rapid two-dimensional exploration of a new series of histone deacetylase inhibitors, through Suzuki-Miyaura cross-coupling reactions for the introduction of a second aromatic element, followed by global deprotection and derivatization of the amino group. (C) 2009 Published by Elsevier Ltd.
• INHIBITORS OF HISTONE DEACETYLASE USEFUL FOR THE TREATMENT OR PREVENTION OF HIV INFECTION
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20210403479A1

  公开（公告）日：2021-12-30

  The present invention relates to Compounds of Formula I: and pharmaceutically acceptable salts or prodrug thereof, wherein R 1 , R 2 , R 3 , R 4 and A are as defined herein. The present invention also relates to compositions comprising at least one compound of Formula I, and methods of using the compounds of Formula I for treating or preventing HIV infection in a subject.