(4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone | 136620-80-9

• 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: (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone
• 英文别名: (4R)-4-benzyl-3-[(2R,3S)-2-bromo-3-hydroxy-3-phenylpropanoyl]-1,3-oxazolidin-2-one
• CAS: 136620-80-9
• 化学式: C₁₉H₁₈BrNO₄
• 分子量: 404.26
• InChiKey: GLUZLEMQYPIQCL-ZACQAIPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone 在 palladium on activated charcoal sodium azide 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 7.38h， 生成 methyl (2S,3S)-2-((tert-butyloxycarbonyl)amino)-3-((methanesulfonyl)oxy)-3-phenylpropionate
  参考文献：
  名称：

  Enantioselective routes to protected syn- and anti-.beta.-phenylcysteines

  摘要：

  DOI：

  10.1021/jo00038a048
• 作为产物：
  描述：

  (4R)-3-(溴乙酰基)-4-(苯基甲基)-2-恶唑烷酮 、 苯甲醛 在 三乙胺 作用下， 生成 (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone
  参考文献：
  名称：

  Enantioselective routes to protected syn- and anti-.beta.-phenylcysteines

  摘要：

  DOI：

  10.1021/jo00038a048

文献信息

• Cyclic anti-aggregatory peptides
  申请人：SmithKline Beecham Corporation

  公开号：US05643872A1

  公开（公告）日：1997-07-01

  This invention relates to compounds of the formula: ##STR1## wherein: A' is absent, Asn, Gln, Ala or Abu; A is absent or a D- or L-amino acid chosen from Arg, HArg, (Me.sub.2)Arg, (Et.sub.2)Arg, Abu, Ala, Gly, His, Lys, or an .alpha.-R' substituted derivative thereof, Dtc, Tpr and Pro; B is a D- or L-amino acid chosen from Arg, HArg, NArg, (Me.sub.2)Arg, (Et.sub.2)Arg and Lys or an .alpha.-R' substituted derivative thereof; Q is absent or a D or L amino acid chosen from Tyr, (Alk)Tyr, Phe, (4'W)Phe, HPhe, Phg, Pro, Trp, His, Ser, (Alk)Ser, Thr, (Alk)Thr, (Alk)Cys, (Alk)Pen, Ala, Val, Nva, Met, Leu, Ile, Nle and Nal, or an .alpha.-R' substituted derivative thereof; M is absent or Gly or a D- or L-amino acid chosen from Glu, Phe, Pro, Lys and Ser or, provided n is 1, B-Gly-Glu-Q; W is halogen or Alk; R' is Alk or PhCH.sub.2 ; ##STR2## wherein Z.sub.1 and Z.sub.2 are linked via a covalent bond between L.sup.1 and L.sup.2 ; or Z.sub.1 and Z.sub.2 are, taken together, a covalent bond between the amino terminal residue and the carboxy terminal residue; L.sup.1 and L.sup.2 are --S-- or --(CH.sub.2).sub.p --; X is R.sub.4 R.sub.5 N or H; Y is H, CONR.sub.1 R.sub.2 or CO.sub.2 R.sub.2 ; R.sub.1 and R.sub.2 are H, Alk or (CH.sub.2).sub.p Ar; R.sub.3 and R.sub.3' are H, Alk, (CH.sub.2).sub.p Ar or taken together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; R.sub.4 is H or Alk; R.sub.5 is R.sub.11, R.sub.11 CO, R.sub.11 OCO, R.sub.11 OCH(R.sub.11')CO, R.sub.11 NHCH(R.sub.11')CO, R.sub.11 SCH(R.sub.11')CO, R.sub.11 SO.sub.2 or R.sub.11 SO; R.sub.6 is Alk, OAlk, halogen or X; R.sub.7 is H, Alk, OAlk, halogen or Y; R.sub.8 and R.sub.8' are H, Alk, (CH.sub.2).sub.p Ph, (CH.sub.2).sub.p Nph or taken together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; R.sub.9 is H, Alk or Y; R.sub.10 is H or Alk; R.sub.11 and R.sub.11' are H, C.sub.1-5 alkyl, C.sub.3-7 cycloalkyl, Ar, Ar--C.sub.1-5 alkyl, Ar--C.sub.3-7 cycloalkyl; Ar is phenyl or phenyl substituted by one or two C.sub.1-5 alkyl, trifluoromethyl, hydroxy, C.sub.1-5 alkoxy or halogen groups; n is 1 or 2; q is 0 or 1; and p is 0, 1, 2 or 3; or a pharmaceutically acceptable salt thereof; which are effective for inhibiting platelet aggregation, pharmaceutical compositions for effecting such activity, a method for inhibiting platelet aggregation and clot formation in a mammal, and a method for inhibiting reocclusion of a blood vessel following fibrinolytic therapy.

  这项发明涉及以下式的化合物：##STR1## 其中：A'为不存在，Asn，Gln，Ala或Abu；A不存在或为Arg，HArg，（Me.sub.2）Arg，（Et.sub.2）Arg，Abu，Ala，Gly，His，Lys或其α-R'取代衍生物，Dtc，Tpr和Pro中选择的D-或L-氨基酸；B为Arg，HArg，NArg，（Me.sub.2）Arg，（Et.sub.2）Arg和Lys或其α-R'取代衍生物中选择的D-或L-氨基酸；Q不存在或为Tyr，（Alk）Tyr，Phe，（4'W）Phe，HPhe，Phg，Pro，Trp，His，Ser，（Alk）Ser，Thr，（Alk）Thr，（Alk）Cys，（Alk）Pen，Ala，Val，Nva，Met，Leu，Ile，Nle和Nal或其α-R'取代衍生物中选择的D或L氨基酸；M不存在或为Gly或在n为1时为B-Gly-Glu-Q中选择的D-或L-氨基酸；W为卤素或Alk；R'为Alk或PhCH.sub.2；##STR2## 其中Z.sub.1和Z.sub.2通过L.sup.1和L.sup.2之间的共价键连接；或Z.sub.1和Z.sub.2一起构成氨基末端残基与羧基末端残基之间的共价键；L.sup.1和L.sup.2为--S--或--(CH.sub.2).sub.p--；X为R.sub.4R.sub.5N或H；Y为H，CONR.sub.1R.sub.2或CO.sub.2R.sub.2；R.sub.1和R.sub.2为H，Alk或（CH.sub.2).sub.pAr；R.sub.3和R.sub.3'为H，Alk，（CH.sub.2).sub.pAr或一起为--(CH.sub.2).sub.4--或--(CH.sub.2).sub.5--；R.sub.4为H或Alk；R.sub.5为R.sub.11，R.sub.11CO，R.sub.11OCO，R.sub.11OCH(R.sub.11')CO，R.sub.11NHCH(R.sub.11')CO，R.sub.11SCH(R.sub.11')CO，R.sub.11SO.sub.2或R.sub.11SO；R.sub.6为Alk，OAlk，卤素或X；R.sub.7为H，Alk，OAlk，卤素或Y；R.sub.8和R.sub.8'为H，Alk，（CH.sub.2).sub.pPh，（CH.sub.2).sub.pNph或一起为--(CH.sub.2).sub.4--或--(CH.sub.2).sub.5--；R.sub.9为H，Alk或Y；R.sub.10为H或Alk；R.sub.11和R.sub.11'为H，C.sub.1-5烷基，C.sub.3-7环烷基，Ar，Ar--C.sub.1-5烷基，Ar--C.sub.3-7环烷基；Ar为苯基或被一个或两个C.sub.1-5烷基，三氟甲基，羟基，C.sub.1-5烷氧基或卤素基取代的苯基；n为1或2；q为0或1；p为0，1，2或3；或其药学上可接受的盐；用于抑制血小板聚集的有效化合物，用于实现该活性的药物组合物，用于在哺乳动物中抑制血小板聚集和凝块形成的方法，以及用于防止纤溶疗法后血管再闭塞的方法。
• US5643872A
  申请人：——

  公开号：US5643872A

  公开（公告）日：1997-07-01
• Enantioselective routes to protected syn- and anti-.beta.-phenylcysteines
  作者：M. Amparo Lago、James Samanen、John D. Elliott

  DOI：10.1021/jo00038a048

  日期：1992.6