(R)-(+)-3-(acetoxy)-1-(phenylmethyl)-2,5-pyrrolidinedione | 156150-59-3

• 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: (R)-(+)-3-(acetoxy)-1-(phenylmethyl)-2,5-pyrrolidinedione
• 英文别名: (3R)-1-benzyl-3-acetatoxypyrrolidine-2,5-dione；(R)-3-acetoxy-1-benzyl-2,5-pyrrolidinedione；(3R)-3-acetoxy-1-benzyl-2,5-dioxopyrrolidine；[(3R)-1-benzyl-2,5-dioxopyrrolidin-3-yl] acetate
• CAS: 156150-59-3
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: BMIVTLPISDRDHK-LLVKDONJSA-N

物化性质

• 沸点：
  440.9±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿；乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-3-(acetoxy)-1-(phenylmethyl)-2,5-pyrrolidinedione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以64%的产率得到(R)-(+)-N-苄基-3-羟基吡咯烷
  参考文献：
  名称：

  4-[(Alkylamino)methyl]furo[3,2-c]pyridines: A New Series of Selective .kappa.-Receptor Agonists

  摘要：

  The synthesis of 5-(arylacetyl)-4-[(alkylamino)methyl]furo[3,2-c]pyridines (16-23, 26, 27) and their activities as kappa-opioid receptor agonists are described. kappa-Agonist potency was particularly sensitive to the nature of the basic moiety. In particular, in the rabbit vas deferens (kappa-specific tissue), the 3-pyrrolidinol analogue 17 (IC50 = 2.7 nM) was found to be approximately 5-fold more potent than the corresponding pyrrolidine analogue 16 (IC50 15 nM). In the rat and hamster vasa deferentia (mu-specific and delta-specific tissues, respectively), 17 showed only weak antagonist activity (PKB > 5.5), underlining its selectivity for the kappa-opioid receptor. The major activity for 17 is resident in the 4S,3'S-isomer 26 (rabbit vas deferens IC50 = 1.1 nM). Compound 26 displays excellent antinociceptive activity, as determined in the mouse acetylcholine-induced abdominal constriction test (ED(50) = 0.001 mg/kg, sc).

  DOI：

  10.1021/jm00040a004
• 作为产物：
  描述：

  (2R,3R)-4-(N-benzylcarbamoyl)-2,3-diacetoxybutyric acid 在 palladium on activated charcoal 盐酸 、 氢溴酸 、 氢气 作用下， 以 1,4-二氧六环 、 水 为溶剂， 25.0~50.0 ℃ 、202.65 kPa 条件下， 反应 42.25h， 生成 (R)-(+)-3-(acetoxy)-1-(phenylmethyl)-2,5-pyrrolidinedione
  参考文献：
  名称：

  Practical Synthesis of (R)-1-Benzyl-3-hydroxy-2,5-pyrrolidinedione and Its Acetate from L-Tartaric Acid

  摘要：

  DOI：

  10.3987/com-95-7301

文献信息

• FUSED BENZENE DERIVATIVE AND USE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1553074B1

  公开（公告）日：2014-06-18
• 3-Hydroxypyrrolidine and (3,4)-dihydroxypyrrolidine derivatives: Inhibition of rat intestinal α-glucosidase
  作者：Elisabete P. Carreiro、Patrícia Louro、Gizé Adriano、Romina A. Guedes、Nicholas Vannuchi、Ana R. Costa、Célia M.M. Antunes、Rita C. Guedes、A.J. Burke

  DOI：10.1016/j.bioorg.2014.04.007

  日期：2014.6

  Thirteen pyrrolidine-based iminosugar derivatives have been synthesized and evaluated for inhibition of a-glucosidase from rat intestine. The compounds studied were the non-hydroxy, mono-hydroxy and dihydroxypyrrolidines. All the compounds were N-benzylated apart from one. Four of the compounds had a carbonyl group in the 2,5-position of the pyrrolidine ring. The most promising iminosugar was the trans-3,4-dihydroxypyrrolidine 5 giving an IC50 of 2.97 +/- 0.046 and a K-I of 1.18 mM. Kinetic studies showed that the inhibition was of the mixed type, but predominantly competitive for all the compounds tested. Toxicological assay results showed that the compounds have low toxicity. Docking studies showed that all the compounds occupy the same region as the DNJ inhibitor on the enzyme binding site with the most active compounds establishing similar interactions with key residues. Our studies suggest that a rotation of similar to 90 degrees of some compounds inside the binding pocket is responsible for the complete loss of inhibitory activity.Despite the fact that activity was found only in the mM range, these compounds have served as simple molecular tools for probing the structural features of the enzyme, so that inhibition can be improved in further studies. (C) 2014 Elsevier Inc. All rights reserved.
• Naylor Alan, Judd Duncan B., Scopes David I. C., Hayes Ann G., Birch Phil+, J. Med. Chem, 37 (1994) N 14, S 2138-2144
  作者：Naylor Alan, Judd Duncan B., Scopes David I. C., Hayes Ann G., Birch Phil+

  DOI：——

  日期：——
• Fused benzene derivative and use
  申请人：Shiraishi Mitsuru

  公开号：US20060106067A1

  公开（公告）日：2006-05-18

  The present invention provides a compound represented by the general formula: [wherein Ring A represents an optionally substituted 5- to 8-membered ring, Ring B represents a further optionally substituted 4- to 10-membered ring, Ring C represents a further optionally substituted benzene ring, X 1 represents carbon atom, X 2 represents a carbon atom, an oxygen atom, etc., W represents a nitrogen atom, etc., Y 11 represents a group represented by the formula CR 2 R 3′ (wherein R 2 represents a hydrogen atom, a cyano group, a nitro group, etc., and R 3′ represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), Y 21 represents a group represented by the formula CR 4 R 5′ (wherein R 4 represents a hydrogen atom, a cyano group, a nitro group, etc., and R 5′ represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), etc., and R 1 represents an electron-withdrawing group, respectively. The formula represents a single bond or a double bond] or a salt thereof, which is useful as an androgen receptor modulator.
• US7649001B2
  申请人：——

  公开号：US7649001B2

  公开（公告）日：2010-01-19