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(S)-3-(4-hydroxyphenyl)-2,2-dimethyl-3-phenyl-N-(1,3,4-thiadiazol-2-yl)propanamide | 1025472-96-1

中文名称
——
中文别名
——
英文名称
(S)-3-(4-hydroxyphenyl)-2,2-dimethyl-3-phenyl-N-(1,3,4-thiadiazol-2-yl)propanamide
英文别名
(3S)-3-(4-hydroxyphenyl)-2,2-dimethyl-3-phenyl-N-(1,3,4-thiadiazol-2-yl)propanamide
(S)-3-(4-hydroxyphenyl)-2,2-dimethyl-3-phenyl-N-(1,3,4-thiadiazol-2-yl)propanamide化学式
CAS
1025472-96-1
化学式
C19H19N3O2S
mdl
——
分子量
353.445
InChiKey
BETRLAMNDBJTLO-INIZCTEOSA-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):
    3.8
  • 重原子数:
    25
  • 可旋转键数:
    5
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.21
  • 拓扑面积:
    103
  • 氢给体数:
    2
  • 氢受体数:
    5

反应信息

  • 作为产物:
    描述:
    2-氨基-1,3,4-噻二唑(S)-3-(4-hydroxyphenyl)-2,2-dimethyl-3-phenylpropanoic acid1-氯-N,N,2-三甲基丙烯胺N,N-二异丙基乙胺 作用下, 以 二氯甲烷 为溶剂, 反应 0.5h, 以87%的产率得到(S)-3-(4-hydroxyphenyl)-2,2-dimethyl-3-phenyl-N-(1,3,4-thiadiazol-2-yl)propanamide
    参考文献:
    名称:
    Dimethyl-diphenyl-propanamide Derivatives As Nonsteroidal Dissociated Glucocorticoid Receptor Agonists
    摘要:
    A series of 2,2-dimethyl-3,3-diphenyl-propanamides as novel glucocorticoid receptor modulators is reported. SAR exploration led to the identification of 4-hydroxyphenyl propanamide derivatives displaying good agonist activity in GR-mediated transrepression assays and reduced agonist activity in GR-mediated transactivation assays. Compounds 17 and 30 showed anti-inflammatory activity comparable to prednisolone in the rat carrageenan-induced paw edema model, with markedly decreased side effects with regard to increases in blood glucose and expression of hepatic tyrosine aminotransferase. A hypothetical binding mode accounting for the induction of the functional activity by a 4-hydroxyl group is proposed.
    DOI:
    10.1021/jm100957a
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文献信息

  • MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-kB ACTIVITY AND USE THEREOF
    申请人:Yang Bingwei Vera
    公开号:US20100063051A1
    公开(公告)日:2010-03-11
    Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity including inflammatory and immune diseases, obesity and diabetes having the structure of formula (I) an enantiomer, diastereomer, tautomer, solvate (e.g. a hydrate), or a pharmaceutically-acceptable salt, thereof, wherein: M is selected from alkyl, substituted alkyl, cycloalkyl, aryl, heterocyclo, and heteroaryl, provided that if M is alkyl then R 6 and R 7 taken together with the carbon atom to which they are both attached are selected from a group other than cycloalkyl; Q is selected from (i) hydrogen, C 1 -C 4 alkyl, and substituted C 1 -C 4 alkyl; or (ii) Q and R 6 are combined with the carbon atoms to which they are attached to form a 3- to 6-membered cycloalkyl; or (iii) Q and M a M are combined with the carbon atom(s) to which they are attached to form a 3- to 7-membered ring containing 1-2 heteroatoms which are independently selected from the group consisting of O, S, SO 2 , and N which ring may be optionally substituted with 0-2 R 5 groups or carbonyl; Z is selected from cycloalkyl, heterocyclo, aryl, or heteroaryl; and M a , Z a , R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , and R 22 are as defined herein. Also provided are pharmaceutical compositions and methods of treating metabolic and inflammatory- or immune-associated diseases or disorders using said compounds.
    提供了一些新型非类固醇化合物,其在治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病中非常有用,包括炎症和免疫性疾病、肥胖症和糖尿病,具有以下结构公式(I)的对映体、顺反异构体、互变异构体、溶剂化物(例如水合物)或其医药上可接受的盐,其中:M选自烷基、取代烷基、环烷基、芳基、杂环烷基和杂芳基,但如果M是烷基,则R6和R7与它们都连接的碳原子一起选自环烷基之外的一组;Q选自(i)氢、C1-C4烷基和取代的C1-C4烷基;或(ii)Q和R6与它们连接的碳原子结合形成3-到6-成员的环烷基;或(iii)Q和MaM与它们连接的碳原子结合形成1-2个杂原子(独立于O、S、SO2和N组成)的3-到7-成员的环,该环可以选择性地用0-2个R5基团或羰基取代;Z选自环烷基、杂环烷基、芳基或杂芳基;而Ma、Za、R1、R2、R3、R4、R6、R7和R22如本文所定义。还提供了制药组合物和使用所述化合物治疗代谢和炎症或免疫相关疾病或紊乱的方法。
  • US7968577B2
    申请人:——
    公开号:US7968577B2
    公开(公告)日:2011-06-28
  • [EN] MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-?B ACTIVITY AND USE THEREOF<br/>[FR] MODULATEURS DE RÉCEPTEUR DE GLUCOCORTICOÏDE, D'ACTIVITÉ AP-1 ET/OU NF-?B, ET LEUR UTILISATION
    申请人:BRISTOL MYERS SQUIBB CO
    公开号:WO2008057862A2
    公开(公告)日:2008-05-15
    [EN] Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-?B activity including inflammatory and immune diseases, obesity and diabetes having the structure of formula (I) an enantiomer, diastereomer, tautomer, solvate (e.g. a hydrate), or a pharmaceutically-acceptable salt, thereof, wherein: M is selected from alkyl, substituted alkyl, cycloalkyl, aryl, heterocyclo, and heteroaryl, provided that if M is alkyl then R6 and R7 taken together with the carbon atom to which they are both attached are selected from a group other than cycloalkyl; Q is selected from (i) hydrogen, C1-C4 alkyl, and substituted C1-C4 alkyl; or (ii) Q and R6 are combined with the carbon atoms to which they are attached to form a 3- to 6-membered cycloalkyl; or (iii) Q and MaM are combined with the carbon atom(s) to which they are attached to form a 3- to 7-membered ring containing 1-2 heteroatoms which are independently selected from the group consisting of O, S, SO2, and N which ring may be optionally substituted with 0-2 R5 groups or carbonyl; Z is selected from cycloalkyl, heterocyclo, aryl, or heteroaryl; and Ma, Za, R1, R2, R3, R4, R6, R7, and R22 are as defined herein. Also provided are pharmaceutical compositions and methods of treating metabolic and inflammatory- or immune-associated diseases or disorders using said compounds.
    [FR] L'invention concerne de nouveaux composés non stéroïdiens qui sont utiles pour traiter des maladies associées à la modulation du récepteur de glucocorticoïde, à l'activité d'AP-1 et/ou du NF-?B, y compris des maladies inflammatoires et immunes, l'obésité et le diabète, ayant la structure de formule (I), un énantiomère, un diastéréomère, un tautomère, un solvate (par exemple un hydrate), ou un sel pharmaceutiquement acceptable de ceux-ci, où : M est sélectionné parmi un groupe alkyle, alkyle substitué, cycloalkyle, aryle, hétérocyclo, et hétéroaryle, à condition que si M est un groupe alkyle, alors R6 et R7 pris avec l'atome de carbone sur lequel ils sont fixés, soient sélectionnés dans un groupe autre que cycloalkyle ; Q est sélectionné parmi (i) de l'hydrogène, un groupe alkyle en C1-C4, et un groupe alkyle en C1-C4 substitué ; ou (ii) Q et R6 sont combinés avec les atomes de carbone sur lesquels ils sont fixés pour former un groupe cycloalkyle à 3 à 6 éléments ; ou (iii) Q et M1M sont combinés avec le ou les atomes de carbone sur lesquels ils sont fixés pour former un cycle à 3 à 7 éléments contenant 1 à 2 hétéroatomes qui sont sélectionnés indépendamment dans le groupe constitué de O, S, SO2, et N, lequel cycle peut être substitué facultativement par 0 à 2 groupes R5 ou carbonyle ; z est sélectionné parmi un groupe cycloalkyle, hétérocyclo, aryle, ou hétéroaryle ; et Ma, Za, R1, R2, R3, R4, R5, R6, R7, et R22 sont tels que définis ici. Des compositions pharmaceutiques et des procédés de traitement de maladies ou de troubles inflammatoires et métaboliques ou immuns associés utilisant de tels composés sont également fournis.
  • Dimethyl-diphenyl-propanamide Derivatives As Nonsteroidal Dissociated Glucocorticoid Receptor Agonists
    作者:Bingwei V. Yang、David S. Weinstein、Lidia M. Doweyko、Hua Gong、Wayne Vaccaro、Tram Huynh、Hai-yun Xiao、Arthur M. Doweyko、Lorraine Mckay、Deborah A. Holloway、John E. Somerville、Sium Habte、Mark Cunningham、Michele McMahon、Robert Townsend、David Shuster、John H. Dodd、Steven G. Nadler、Joel C. Barrish
    DOI:10.1021/jm100957a
    日期:2010.12.9
    A series of 2,2-dimethyl-3,3-diphenyl-propanamides as novel glucocorticoid receptor modulators is reported. SAR exploration led to the identification of 4-hydroxyphenyl propanamide derivatives displaying good agonist activity in GR-mediated transrepression assays and reduced agonist activity in GR-mediated transactivation assays. Compounds 17 and 30 showed anti-inflammatory activity comparable to prednisolone in the rat carrageenan-induced paw edema model, with markedly decreased side effects with regard to increases in blood glucose and expression of hepatic tyrosine aminotransferase. A hypothetical binding mode accounting for the induction of the functional activity by a 4-hydroxyl group is proposed.
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