N-(4-fluorophenylsulfonyl)-D-valine | 190275-60-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(4-fluorophenylsulfonyl)-D-valine
• 英文别名: N-(4-fluorobenzenesulfonyl)valine；N-[(4-fluorophenyl)sulfonyl]-D-valine；D-Valine, N-[(4-fluorophenyl)sulfonyl]-；(2R)-2-[(4-fluorophenyl)sulfonylamino]-3-methylbutanoic acid
• CAS: 190275-60-6
• 化学式: C₁₁H₁₄FNO₄S
• 分子量: 275.301
• InChiKey: VNRQLAGSSZUTTO-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-fluorophenylsulfonyl)-D-valine 在 pyridine-SO3 complex 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.67h， 生成 N-(4-fluorophenylsulfonyl)-D-valyl-D-leucinal
  参考文献：
  名称：

  Structure−Activity Relationship Study and Drug Profile of N-(4-Fluorophenylsulfonyl)-l-valyl-l-leucinal (SJA6017) as a Potent Calpain Inhibitor

  摘要：

  Novel N-arylsulfonyldipeptidyl aldehyde derivatives were prepared by DMSO oxidation from the corresponding dipeptide alcohol, and their potencies as calpain inhibitors were evaluated in vitro. Among them, N-(4-fluorophenylsulfonyl)-L-valyl-L-leucinal (8, SJA6017) potently inhibited calpains. 8 also inhibited cathepsin B and L but did not inhibit other cysteine proteases (interleukin 1beta-converting enzyme), serine proteases (trypsin, chymotrypsin, thrombin, factor VIIa, factor Xa), or proteasome. Preliminary cytotoxicity studies of 8 exhibited a relatively safe profile.

  DOI：

  10.1021/jm0201924
• 作为产物：
  描述：

  2-氧代-3-甲基丁酸 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 甲烷磺酸 、 氢气 、 三乙胺 、 4,4'-bis(diphenylphosphino)-2,2',5,5'-tetramethyl-3,3'-bithiophene 作用下， 以 乙醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 25.0 ℃ 、620.53 kPa 条件下， 反应 48.0h， 生成 N-(4-fluorophenylsulfonyl)-D-valine
  参考文献：
  名称：

  Asymmetric Hydrogenation of N-Sulfonylated-α-dehydroamino Acids:  Toward the Synthesis of an Anthrax Lethal Factor Inhibitor

  摘要：

  [GRAPHIC]A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated-alpha-dehydroamino acids has been discovered and demonstrated in the synthesis of an anthrax lethal factor inhibitor (LFI). Herein, this methodology is used to prepare N-sulfonylated amino acids in up to 98% ee. This unprecedented hydrogenation uses a chiral Ru catalyst rather than Rh as typical for acylated dehydroamino acids and esters, and this work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst.

  DOI：

  10.1021/ol050869s

文献信息

• Thioaryl sulfonamide hydroxamic acid compounds
  申请人：——

  公开号：US06087359A1

  公开（公告）日：2000-07-11

  A thioaryl sulfonamide hydroxamic acid compound that inter alia inhibits matrix metalloprotease activity is disclosed as are a treatment process that comprises administering a contemplated thioaryl sulfonamide hydroxamic acid compound in a MMP enzyme-inhibiting effective amount to a host having a condition associated with pathological matrix metalloprotease activity.

  本文披露了一种硫芳基磺酰胺羟肟酸化合物，该化合物在抑制基质金属蛋白酶活性方面起作用，还披露了一种治疗过程，包括向患有与病理性基质金属蛋白酶活性相关的病症的宿主施用所考虑的硫芳基磺酰胺羟肟酸化合物，施用剂量为MMP酶抑制有效量。
• [EN] PROCESS FOR MAKING N-SULFONATED-AMINO ACID DERIVATIVES<br/>[FR] PROCEDE DE FABRICATION DE DERIVES D'ACIDES AMINES N-SULFONES
  申请人：MERCK & CO INC

  公开号：WO2005118529A3

  公开（公告）日：2006-02-16
• THIOARYL SULFONAMIDE HYDROXAMIC ACID COMPOUNDS
  申请人：MONSANTO COMPANY

  公开号：EP0977745A1

  公开（公告）日：2000-02-09
• US6087359A
  申请人：——

  公开号：US6087359A

  公开（公告）日：2000-07-11
• [EN] THIOARYL SULFONAMIDE HYDROXAMIC ACID COMPOUNDS<br/>[FR] COMPOSES D'ACIDE HYDROXAMIQUE SULFONAMIDE THIOARYLE
  申请人：MONSANTO COMPANY

  公开号：WO1998039313A1

  公开（公告）日：1998-09-11

  (EN) A thioaryl sulfonamide hydroxamic acid compound that inter alia inhibits matrix metalloprotease activity is disclosed as are a treatment process that comprises administering a contemplated thioaryl sulfonamide hydroxamic acid compound in a MMP enzyme-inhibiting effective amount to a host having a condition associated with pathological matrix metalloprotease activity.(FR) La présente invention concerne un composé d'acide hydroxamique sulfonamide thioaryle qui inhibe notamment une activité de métalloprotéase matricielle (MMP). La présente invention concerne également un procédé de traitement qui consiste à administer le composé d'acide hydroxamique sulfonamide thiaryle en question, à raison d'une dose efficace destinée à inhiber l'activité d'une enzyme MMP, à un hôte présentant une condition associée à une activité pathologique de métalloprotéase matricielle.