methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate | 136620-77-4

• 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: methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate
• 英文别名: methyl (2R,3S)-3-(acetylthio)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionate；methyl(2R,3S)3-(acetylthio)2-((tert-butyloxycarbonyl)amino)-3-phenylpropionate；methyl (2R,3S)-3-acetylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
• CAS: 136620-77-4
• 化学式: C₁₇H₂₃NO₅S
• 分子量: 353.439
• InChiKey: ZCPNZUZYGIHUGJ-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate 在 sodium hydroxide 作用下， 反应 0.5h， 生成 methyl(2R,3S)-2-((tert-butyloxycarbonyl)amino)-3-mercapto-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：

  (S)-4-Benzyl-3-((4S,5R)-5-phenyl-2-thioxo-oxazolidine-4-carbonyl)-oxazolidin-2-one 在 lithium hydroxide 、 甲酸 、 双氧水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 硫代乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.5h， 生成 methyl (2R,3S)-3-(acetylthio)-2-((tert-butoxycarbonyl)amino)-3-phenylpropionate
  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.

  本发明涉及以下式的化合物：## STR1 ## 其中：A'不存在，Asn，Gln，Ala或Abu；A不存在或为D-或L-氨基酸，选择自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; B为D-或L-氨基酸，选择自Arg，HArg，NArg，（Me.sub.2）Arg，（Et.sub.2）Arg和Lys或其α-R'取代衍生物; Q不存在或为D或L氨基酸，选择自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; M不存在或为Gly或D-或L-氨基酸，选择自Glu，Phe，Pro，Lys和Ser或，如果n为1，则为B-Gly-Glu-Q; 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.2一起取自氨基末端残基和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.4 R.sub.5 N或H; Y为H，CONR.sub.1 R.sub.2或CO.sub.2 R.sub.2; R.sub.1和R.sub.2为H，Alk或（CH.sub.2）.sub.p Ar; R.sub.3和R.sub.3'为H，Alk，（CH.sub.2）.sub.p Ar或一起取为--（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.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或R.sub.11 SO; 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.p Ph，（CH.sub.2）.sub.p Nph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。它们对抑制血小板聚集有效，制备此类活性的药物组合物，一种抑制哺乳动物中血小板聚集和血栓形成的方法，以及一种抑制纤溶疗法后血管再闭塞的方法。
• 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