3-(3-cyclopropyl-1-oxopropyl)-4(S)-phenylmethyl-2-oxazolidinone | 155295-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-(3-cyclopropyl-1-oxopropyl)-4(S)-phenylmethyl-2-oxazolidinone
• 英文别名: (4S)-3-(3-cyclopropyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone；(S)-4-benzyl-3-(3-cyclopropylpropanoyl)oxazolidin-2-one；(S)-4-Benzyl-3-(3-cyclopropyl-propionyl)-oxazolidin-2-one；(4S)-4-benzyl-3-(3-cyclopropylpropanoyl)-1,3-oxazolidin-2-one
• CAS: 155295-65-1
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: SNVWYQBGGSCYPI-AWEZNQCLSA-N

物化性质

• 沸点：
  446.4±14.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-cyclopropyl-1-oxopropyl)-4(S)-phenylmethyl-2-oxazolidinone 在 2,6-二甲基吡啶 、 lithium hydroxide 、 正丁基锂 、 双氧水 、 potassium carbonate 、 二异丙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 38.5h， 生成 (2R,4S,5R)-4,5-di(tert-butyldimethylsilyloxy)-2-(cyclopropylmethyl)-6-phenylhexanoic acid
  参考文献：
  名称：

  Novel small renin inhibitors containing 4,5- or 3,5-dihydroxy-2-substituted-6-phenylhexanamide replacements at the P2P3 sites

  摘要：

  Renin inhibitors containing a 4,5- or a 3,5-dihydroxy-2-substituted-6-phenylhexanamide fragment at the P-2- P-3 Sites have been prepared and evaluated. The four possible diastereomeric diols of the two series of inhibitors were synthesized to determine the optimal configuration of the carbinol centers for these replacements. The most potent inhibitors of each series, 1a and 2c have a molecular weight of only 503 and IC50 values of 23 and 20 nM in a human plasma renin assay at pH 6.0. Their very low aqueous solubility limited their further evaluation. The efficacy of these P-2-P-3 replacements is a result of their ability to maintain the important hydrogen-bonds with the enzyme. Due to conformational differences with the dipeptide, adjustment at the P-2 Side chain was required. These 4,5- and 3,5-dihydroxyhexanamide segments could be seen as novel N-terminal dipeptide replacements. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)80011-4
• 作为产物：
  描述：

  (S)-4-benzyl-2-oxazolidinone lithium salt 在 palladium diacetate 、 三甲基乙酰氯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 3-(3-cyclopropyl-1-oxopropyl)-4(S)-phenylmethyl-2-oxazolidinone
  参考文献：
  名称：

  4-Amino-2-alkyl-butyramides as small molecule CCR2 antagonists with favorable pharmacokinetic properties

  摘要：

  A systematic examination of the central aromatic portion of the lead (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-(4-fluorophenyl)-4-(1'H-spiro[indene-1,4'-piperidin]-1'-yl)butanamide (9) led to the discovery of a novel class of CCR2 receptor antagonists, which carry small alicyclic groups such as cyclopropyl, cylobutyl, or cyclopropylmethyl attached at C-2 of the carbon backbone. The most potent compound discovered, namely (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-cyclopropyl-4-[(1R,3'R)-3'-methyl-1'H-spiro[indene-1,4'-piperidin]-1'-yl]butanamide (29), showed very high binding affinity (IC50 = 4 nM, human monocyte) and excellent selectivity toward other related chemokine receptors. The excellent pharmacokinetic profile of this new lead compound allows for extensive in vivo evaluation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.011

文献信息

• [EN] NOVEL COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERS<br/>[FR] NOUVEAUX COMPOSÉS, LEURS COMPOSITIONS PHARMACEUTIQUES ET MÉTHODES D'UTILISATION DANS LE TRAITEMENT DE TROUBLES MÉTABOLIQUES
  申请人：EUROSCREEN SA

  公开号：WO2011151434A1

  公开（公告）日：2011-12-08

  The present invention is directed to novel compounds of formula (I) and their use in treating metabolic diseases.

  本发明涉及公式（I）的新化合物及其在治疗代谢性疾病中的应用。
• Renin inhibiting polyhydroxy-monoamides
  申请人：Bio-Mega, Inc.

  公开号：US05354767A1

  公开（公告）日：1994-10-11

  Disclosed herein are compounds of the formula: R.sup.1 CH.sub.2 CH(X)CH(Y)CH(Z)CHR.sup.2 C(O)NHCHR.sup.3 CH(OH)CH(OH)R.sup.4 wherein R.sup.1 is a terminal unit, for example lower cycloalkyl or phenyl; R.sup.2 is, for example, an optionally substituted alkyl, cycloalkylmethyl, benzyl, 4-imidazolylmethyl, 2-thienylmethyl or 4-thiazolylmethyl; R.sup.3 is alkyl, cycloalkylmethyl or an optionally substituted benzyl; R.sup.4 is alkyl or cycloalkyl; and X and Y each is hydroxy and Z is hydrogen, or X and Z each is hydroxy and Y is hydrogen; with the provisos that (a) the carbon atom bearing R.sup.2 has the "R" configuration except when R.sup.2 is 2-thienylmethyl or 2-thiazolylmethyl, X and Y each is hydroxy and Z is hydrogen, then the carbon atom bearing R.sup.2 has the "S" configuration; (b) the carbon atoms bearing R.sup.3 and R.sup.4 each has the "S" configuration; and (c) the carbon atom located between the last-said two carbon atoms has the "R" configuration. The compounds inhibit renin activity and are indicated for the treatment of hypertension and congestive heart failure.

  本文所述的化合物的化学式为：R.sup.1 CH.sub.2 CH（X）CH（Y）CH（Z）CHR.sup.2 C（O）NHCHR.sup.3 CH（OH）CH（OH）R.sup.4，其中R.sup.1是末端基，例如较低的环烷基或苯基；R.sup.2是例如可选取代的烷基，环烷基甲基，苄基，4-咪唑基甲基，2-噻吩基甲基或4-噻唑基甲基；R.sup.3是烷基，环烷基甲基或可选取代的苄基；R.sup.4是烷基或环烷基；X和Y各为羟基，Z为氢，或X和Z各为羟基，Y为氢；但需满足以下条件：（a）承载R.sup.2的碳原子具有“R”构型，除非R.sup.2为2-噻吩基甲基或2-噻唑基甲基，X和Y各为羟基，Z为氢，则承载R.sup.2的碳原子具有“S”构型；（b）承载R.sup.3和R.sup.4的碳原子各具有“S”构型；（c）位于上述两个碳原子之间的碳原子具有“R”构型。这些化合物能够抑制肾素活性，适用于治疗高血压和充血性心力衰竭。
• LACTAMS SUBSTITUTED BY CYCLIC SUCCINATES AS INHIBITORS OF ABETTA PROTEIN PRODUCTION
  申请人：Olson E. Richard

  公开号：US20080103128A1

  公开（公告）日：2008-05-01

  This invention relates to novel lactams having the Formula (I): to their pharmaceutical compositions and to their methods of use. These novel compounds inhibit the processing of amyloid precursor protein and, more specifically, inhibit the production of Aβ-peptide, thereby acting to prevent the formation of neurological deposits of amyloid protein. More particularly, the present invention relates to the treatment of neurological disorders related to β-amyloid production such as Alzheimer's disease and Down's Syndrome.

  本发明涉及具有式(I)的新型内酰胺，它们的制药组合物和使用方法。这些新型化合物抑制淀粉样前体蛋白的加工，更具体地说，抑制Aβ肽的产生，从而防止神经沉积物的淀粉样蛋白形成。更具体地，本发明涉及与β-淀粉样蛋白产生相关的神经系统疾病的治疗，例如阿尔茨海默病和唐氏综合症。
• LACTAMS SUBSTITUTED BY CYCLIC SUCCINATES AS INHIBITORS OF Abeta PROTEIN PRODUCTION
  申请人：Olson Richard E.

  公开号：US20090062256A1

  公开（公告）日：2009-03-05

  This invention relates to novel lactams having the Formula (I): to their pharmaceutical compositions and to their methods of use. These novel compounds inhibit the processing of amyloid precursor protein and, more specifically, inhibit the production of Aβ-peptide, thereby acting to prevent the formation of neurological deposits of amyloid protein. More particularly, the present invention relates to the treatment of neurological disorders related to β-amyloid production such as Alzheimer's disease and Down's Syndrome.

  本发明涉及具有公式（I）的新型内酰胺、它们的制药组合物以及它们的使用方法。这些新型化合物抑制淀粉样前体蛋白的处理，更具体地抑制Aβ-肽的产生，从而防止神经沉积物的淀粉样蛋白形成。更具体地，本发明涉及与β-淀粉样蛋白产生相关的神经系统疾病的治疗，例如阿尔茨海默病和唐氏综合症。
• MACROCYCLIC INHIBITORS OF FLAVIVIRIDAE VIRUSES
  申请人：Selcia Ltd.

  公开号：US20140030221A1

  公开（公告）日：2014-01-30

  Provided are compounds of Formula I: and pharmaceutically acceptable salts and esters thereof. The compounds, compositions, and methods provided are useful for the treatment of virus infections, particularly hepatitis C infections.

  提供了I式化合物及其药学上可接受的盐和酯。所提供的化合物、组合物和方法对于治疗病毒感染，特别是丙型肝炎感染具有有用性。