N-(2-methylpropyl)-N-[(3S)-2-oxoazepan-3-yl]benzenesulfonamide | 449807-06-1

• 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-(2-methylpropyl)-N-[(3S)-2-oxoazepan-3-yl]benzenesulfonamide
• CAS: 449807-06-1
• 化学式: C₁₆H₂₄N₂O₃S
• 分子量: 324.444
• InChiKey: FSJMSJDGTBXLRQ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-methylpropyl)-N-[(3S)-2-oxoazepan-3-yl]benzenesulfonamide 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 Nα-Isobutyl-Nα-benzenesulfonyl-Nε-(9-fluorenylmethoxycarbonyl)-L-lysine
  参考文献：
  名称：

  Lysine derivatives as potent HIV protease inhibitors. Discovery, synthesis and structure–activity relationship studies

  摘要：

  A screening assay program on HIV-protease was carried out on more than fifty commercially available N-protected amino acids and has revealed that those with a long side chain such as lysine, ornithine and arginine exhibited significant inhibition of HIV protease enzyme. The presence of an Fmoc group was found to be essential to obtain micromolar inhibitors and the addition of an alkyl group at the N alpha-position resulted in the discovery of the lead compound 11 displaying a 5 nM inhibition constant. Although this new inhibitor series is not categorized among those mimicking the substrate with a non-hydrolyzable transition-state isoster, it was found very specific to inhibit HIV protease enzyme in comparison to the mammalian aspartyl proteases pepsin, renin and cathepsin. Furthermore, these inhibitors did not show any cytotoxicity at a concentration below 75 mu M. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.068
• 作为产物：
  描述：

  (S)-3-氨基-2-己内酰胺 在 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-(2-methylpropyl)-N-[(3S)-2-oxoazepan-3-yl]benzenesulfonamide
  参考文献：
  名称：

  Lysine derivatives as potent HIV protease inhibitors. Discovery, synthesis and structure–activity relationship studies

  摘要：

  A screening assay program on HIV-protease was carried out on more than fifty commercially available N-protected amino acids and has revealed that those with a long side chain such as lysine, ornithine and arginine exhibited significant inhibition of HIV protease enzyme. The presence of an Fmoc group was found to be essential to obtain micromolar inhibitors and the addition of an alkyl group at the N alpha-position resulted in the discovery of the lead compound 11 displaying a 5 nM inhibition constant. Although this new inhibitor series is not categorized among those mimicking the substrate with a non-hydrolyzable transition-state isoster, it was found very specific to inhibit HIV protease enzyme in comparison to the mammalian aspartyl proteases pepsin, renin and cathepsin. Furthermore, these inhibitors did not show any cytotoxicity at a concentration below 75 mu M. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.068

文献信息

• Protease Inhibitors
  申请人：Stranix Brent Richard

  公开号：US20100184974A1

  公开（公告）日：2010-07-22

  The present invention provides HIV protease inhibitors of formulas I, IA, IB, Ib or II, or pharmaceutically acceptable salts thereof, wherein R 2 may be, for example, 2-pyridyl-CH 2 —, 3-pyridyl-CH 2 —, 4-pyridyl-CH 2 —, a sulfonyl group as described in the formulas herein including benzenesulfonyl or thiophenesulfonyl groups, R 2a —CO)—, R 2a being selected from the group consisting of piperonyl, 2-pyranzinyl (unsubstituted or substituted with H, or an alkyl of 1 to 4 carbon atoms) or a picolylamine group as described herein, wherein R3 may be, for example, a phenyl group or diphenylmethyl group as described herein, and wherein Cx may be, for example, COOH, CONR 5 R 6 , CH 2 OH or CH 2 OR 7 .

  本发明提供了公式I、IA、IB、Ib或II的HIV蛋白酶抑制剂，或其药学上可接受的盐，其中R2可能是，例如，2-吡啶基-CH2—，3-吡啶基- —，4-吡啶基- —，如本文中所述的磺酰基，包括苯磺酰基或噻吩磺酰基，R2a—CO)—，R2a选自由本文中所述的吡哌啶基、2-吡啶基（未取代或取代为H，或1至4个碳原子的烷基）或本文中所述的吡哌啶胺基，其中R3可能是，例如，本文中所述的苯基或二苯甲基基团，Cx可能是，例如，COOH、CONR5R6、 OH或 OR7。
• PROTEASE INHIBITORS
  申请人：TaiMed Biologics, Inc.

  公开号：US20130158261A1

  公开（公告）日：2013-06-20

  The present invention provides HIV protease inhibitors of formulas I, IA, IB, Ib or II, or pharmaceutically acceptable salts thereof, wherein R 2 may be, for example, 2-pyridyl-CH 2 —, 3-pyridyl-CH 2 —, 4-pyridyl-CH 2 —, a sulfonyl group as described in the formulas herein including benzenesulfonyl or thiophenesulfonyl groups, R 2a —CO)—, R 2a being selected from the group consisting of piperonyl, 2-pyranzinyl (unsubstituted or substituted with H, or an alkyl of 1 to 4 carbon atoms) or a picolylamine group as described herein, wherein R3 may be, for example, a phenyl group or diphenylmethyl group as described herein, and wherein Cx may be, for example, COOH, CONR 5 R 6 , CH 2 OH or CH 2 OR 7 .

  本发明提供了式I、IA、IB、Ib或II的HIV蛋白酶抑制剂，或其药学上可接受的盐，其中R2可以是例如2-吡啶基-CH2-、3-吡啶基- -、4-吡啶基- -、如本公式中所述的磺酰基，包括苯磺酰基或噻吩磺酰基，R2a-CO-，其中R2a是从所述的吡哆酰基、2-吡咯啉基（未取代或取代有1至4个碳原子的烷基）或如本文所述的哌啶基氨基中选择的，其中R3可以是例如如本文所述的苯基或二苯甲基基团，Cx可以是例如COOH、CONR5R6、 OH或 OR7。
• US6632816B1
  申请人：——

  公开号：US6632816B1

  公开（公告）日：2003-10-14
• US8410300B2
  申请人：——

  公开号：US8410300B2

  公开（公告）日：2013-04-02
• US8742158B2
  申请人：——

  公开号：US8742158B2

  公开（公告）日：2014-06-03