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{(1S,2R)-3-[(4-Aminomethyl-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester | 253266-00-1

中文名称
——
中文别名
——
英文名称
{(1S,2R)-3-[(4-Aminomethyl-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester
英文别名
Carbamic acid, [(1S,2R)-3-[[[4-(aminomethyl)phenyl]sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-, (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester;[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-4-[[4-(aminomethyl)phenyl]sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
{(1S,2R)-3-[(4-Aminomethyl-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester化学式
CAS
253266-00-1
化学式
C28H39N3O7S
mdl
——
分子量
561.7
InChiKey
DQTQCTYWNGZNQX-UIPNDDLNSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.5
  • 重原子数:
    39
  • 可旋转键数:
    13
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.54
  • 拓扑面积:
    149
  • 氢给体数:
    3
  • 氢受体数:
    9

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    {(1S,2R)-3-[(4-Aminomethyl-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) esterN-[(1,1-二甲基乙氧基)羰基]-L-缬氨酰-L-脯氨酸N-羟基-7-氮杂苯并三氮唑盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下, 以 DMF (N,N-dimethyl-formamide) 为溶剂, 反应 20.0h, 以55%的产率得到tert-butyl N-[(2S)-1-[(2S)-2-[[4-[[(2R,3S)-3-[[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl]oxycarbonylamino]-2-hydroxy-4-phenylbutyl]-(2-methylpropyl)sulfamoyl]phenyl]methylcarbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
    参考文献:
    名称:
    [EN] PRODRUGS CLEAVABLE BY CD26
    [FR] PROMEDICAMENTS POUVANT ETRE CLIVES A MOYEN DE CD26
    摘要:
    本发明提供了一种新的前药技术和新的前药,以增加药物的溶解度,调节血浆蛋白结合或增强药物的生物利用度。在本发明中,前药是治疗化合物和肽(例如四肽或六肽)的结合物,其中结合物可被二肽肽酶(更优选为CD26,也称为DPPIV,即二肽氨二肽酶IV)水解。本发明还提供了一种生产所述前药的方法,以增强药物在大脑和淋巴系统中的传递,并/或延长药物在血浆中的半衰期。
    公开号:
    WO2004098644A1
  • 作为产物:
    参考文献:
    名称:
    Discovery and Selection of TMC114, a Next Generation HIV-1 Protease Inhibitor
    摘要:
    The screening of known HIV-1 protease inhibitors against a panel of multi-drug-resistant viruses revealed the potent activity of TMC126 on drug-resistant mutants. In comparison to amprenavir, the improved affinity of TMC126 is largely the result of one extra hydrogen bond to the backbone of the protein in the P2 pocket. Modification of the substitution pattern on the phenylsulfonamide P2 ' substituent of TMC126 created an interesting SAR, with the close analogue TMC114 being found to have a similar antiviral activity against the mutant and the wild-type viruses. X-ray and thermodynamic studies on both wild-type and mutant enzymes showed an extremely high enthalpy driven affinity of TMC114 for HIV-1 protease. In vitro selection of mutants resistant to TMC 114 starting from wild-type virus proved to be extremely difficult; this was not the case for other close analogues. Therefore, the extra H-bond to the backbone in the P2 pocket cannot be the only explanation for the interesting antiviral profile of TMC114. Absorption studies in animals indicated that TMC114 has pharmacokinetic properties comparable to currently approved HIV-1 protease inhibitors.
    DOI:
    10.1021/jm049560p
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文献信息

  • PROCESS FOR SYNTHESIS OF SYN AZIDO EPOXIDE AND ITS USE AS INTERMEDIATE FOR THE SYNTHESIS OF AMPRENAVIR & SAQUINAVIR
    申请人:Council of Scientific & Industrial Research
    公开号:US20150011782A1
    公开(公告)日:2015-01-08
    Disclosed herein is a novel route of synthesis of syn azide epoxide of formula 5, which is used as a common intermediate for asymmetric synthesis of HIV protease inhibitors such as Amprenavir, Fosamprenavir, Saquinavir and formal synthesis of Darunavir and Palinavir obtained by Cobalt-catalyzed hydrolytic kinetic resolution of racemic anti-(2SR,3SR)-3-azido-4-phenyl-1,2-epoxybutane (azido-epoxide).
    本文披露了一种合成公式5的syn叠氮环氧化物的新路线,该化合物被用作HIV蛋白酶抑制剂的不对称合成的常见中间体,如Amprenavir、Fosamprenavir、Saquinavir以及通过钴催化的拆分手性反式-(2SR,3SR)-3-叠氮-4-苯基-1,2-环氧丁烷(叠氮环氧化物)合成Darunavir和Palinavir。
  • Prodrugs Cleavable by Cd26
    申请人:Balzarini Jan
    公开号:US20070275900A1
    公开(公告)日:2007-11-29
    The present invention provides a new prodrug technology and new prodrugs in order to increase the solubility, to modulate plasma protein binding or to enhance the biovailability of a drug. In the present invention the prodrugs are conjugates of a therapeutic compound and a peptide (eg tetrapeptide or hexapeptide) wherein the conjugate is cleavable by dipeptidyl-peptidases, more preferably by CD26, also known as DPPIV (dipeptidyl aminodipeptidase IV). The present invention furthermore provides a method of producing said prodrugs, to enhance brain and lymphatic delivery of drugs and/or to extend drug half-lives in plasma.
    本发明提供了一种新的前药技术和新的前药,以增加药物的溶解度,调节血浆蛋白结合或增强药物的生物利用度。在本发明中,前药是治疗化合物和肽(例如四肽或六肽)的结合物,其中结合物可被二肽基-肽酶(更好地是CD26,也称为DPPIV(二肽基氨肽酰二肽酶IV))水解。本发明还提供了一种生产所述前药的方法,以增强药物在脑和淋巴中的递送和/或延长药物在血浆中的半衰期。
  • [EN] METHOD AND COMPOSITIONS FOR TREATING HIV INFECTIONS<br/>[FR] PROCÉDÉ ET COMPOSITIONS UTILISÉS POUR TRAITER LES INFECTIONS À VIH
    申请人:PURDUE RESEARCH FOUNDATION
    公开号:WO2008133734A4
    公开(公告)日:2009-02-12
  • Hiv Prodrugs Cleavable by Cd26
    申请人:De Kock Herman Augustinus
    公开号:US20080214648A1
    公开(公告)日:2008-09-04
    The present invention provides new prodrugs which are conjugates of a therapeutic compound and a peptide wherein the conjugate is cleavable by dipeptidyl-peptidases, more preferably by CD26, also known as DPPIV (dipeptidyl aminodipeptidase IV). The present prodrugs have the formula the stereoisomeric forms and salts thereof, wherein n is 1 to 5; Y is proline, alanine, hydroxyproline, dihydroxyproline, thiazolidinecarboxylic acid (thioproline), dehydroproline, pipecolic acid (L-homoproline), azetidinecarboxylic acid, aziridinecarboxylic acid, glycine, serine, valine, leucine, isoleucine and threonine; X is selected from any amino acid in the D- or L-configuration; X and Y in each repeat of [Y-X] are chosen independently from one another and independently from other repeats; Z is a direct bond or a bivalent straight or branched saturated hydrocarbon group having from 1 to 4 carbon atoms; R 1 is an aryl, heteroaryl, aryloxy, heteroaryloxy, aryloxyC 1-4 alkyl, heterocycloalkyloxy, heterocycloalkylC 1-4 alkyloxy, heteroaryloxyC 1-4 alkyl, heteroarylC 1-4 alkyloxy; R 2 is arylC 1-4 alkyl; R 3 is C 1-10 alkyl, C 2-6 alkenyl or C 3-7 cycloalkylC 1-4 alkyl; R 4 is hydrogen or C 1-4 alkyl. The present invention furthermore provides the use of said prodrugs as medicines as well as a method of producing said prodrugs.
  • US8236756B2
    申请人:——
    公开号:US8236756B2
    公开(公告)日:2012-08-07
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