phenylmethyl <2-<4-<(2,4-dioxo-5-thiazolidinyl)methyl>phenoxy>ethyl>methylcarbamate | 142649-75-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenylmethyl <2-<4-<(2,4-dioxo-5-thiazolidinyl)methyl>phenoxy>ethyl>methylcarbamate
• 英文别名: benzyl (2-(4-((2,4-dioxothiazolidin-5-yl)methyl)phenoxy)ethyl)(methyl)carbamate；benzyl N-[2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]ethyl]-N-methylcarbamate
• CAS: 142649-75-0
• 化学式: C₂₁H₂₂N₂O₅S
• 分子量: 414.482
• InChiKey: HJKZAEPVTVPOID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenylmethyl <2-<4-<(2,4-dioxo-5-thiazolidinyl)methyl>phenoxy>ethyl>methylcarbamate 在 盐酸 作用下， 以 乙醇 为溶剂， 以49%的产率得到5-{4-[2-(methylamino)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents

  摘要：

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.

  DOI：

  10.1021/jm00049a017
• 作为产物：
  描述：

  (2-羟基乙基)甲基氨基甲酸苄酯 在 palladium on activated charcoal 氢气 、 哌啶鎓苯甲酸盐 、 sodium hydride 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 生成 phenylmethyl <2-<4-<(2,4-dioxo-5-thiazolidinyl)methyl>phenoxy>ethyl>methylcarbamate
  参考文献：
  名称：

  [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents

  摘要：

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.

  DOI：

  10.1021/jm00049a017

文献信息

• Incorporation of a coumarin unit by nucleophilic addition reaction into a PPARγ ligand
  作者：Chisato Yoshikawa、Hiroaki Ishida、Toshimasa Itoh

  DOI：10.1016/j.tetlet.2020.151842

  日期：2020.5

  We examined the incorporation of a coumarin unit into model compounds using nucleophilic addition reaction. Then we applied these conditions to synthesize coumarin-incorporated Rosiglitazone. This fluorescent labeled compound maintained transcriptional activity for PPARγ.

  我们检查了使用亲核加成反应将香豆素单元掺入模型化合物中。然后，我们将这些条件应用于合成香豆素的罗格列酮。该荧光标记的化合物保持了对PPARγ的转录活性。
• THIAZOLIDINE DIONE DERIVATIVES
  申请人：BEECHAM GROUP plc

  公开号：EP0555251A1

  公开（公告）日：1993-08-18
• [EN] THIAZOLIDINE DIONE DERIVATIVES
  申请人：BEECHAM GROUP PLC

  公开号：WO1992007838A1

  公开（公告）日：1992-05-14

  (EN) A compound of formula (I) or a tautomeric form thereof and/or a pharmaceutically acceptable salt thereof, and/or a pharmaceutically acceptable solvate thereof, wherein: A1 represents an alkyl group, a substituted or unsubstituted aryl group or an aralkyl group wherein the alkylene or the aryl moiety may be substituted or unsubstituted; A2 represents a benzene ring having in total up to three optional substituents; R1 represents a hydrogen atom, an alkyl group, an acyl group, an aralkyl group wherein the alkyl or the aryl moiety may be substituted or unsubstituted, or a substituted or unsubstituted aryl group; or A1 together with R1 represents substituted or unsubstituted C2-3 polymethylene group, optional substituents for the polymethylene group being selected from alkyl or aryl or adjacent substituents together with the methylene carbon atoms to which they are attached form a substituted or unsubstituted phenylene group; R2 and R3 each represent hydrogen, or R2 and R3 together represent a bond; X represents O or S; and n represents an integer in the range of from 2 to 6; a process for preparing such a compound, a composition comprising such a compound and the use of such a compound or composition in medicine.(FR) L'invention se rapporte à un composé représenté par la formule (I) ou à une forme tautomère de ce composé et/ou un sel pharmaceutiquement acceptable et/ou un solvate pharmaceutiquement acceptable de ce composé. Dans la formule (I), A1 représente un groupe alkyle, un groupe aryle substitué ou non ou un groupe aralkyle dans lequel l'alkylène ou la fraction aryle peut être substitué ou non; A2 représente une chaîne fermée de benzène ayant au total jusqu'à trois substituants optionnels; R1 représente un atome d'hydrogène, un groupe alkyle, un groupe acyle, un groupe aralkyle dans lequel l'alkyle ou la fraction aryle peut être substitué ou non ou un groupe aryle substitué ou non; ou R1 représente, conjointement avec R1, un groupe polyméthylène C2-3 substitué ou non, les substituants optionnels pour le groupe polyméthylène étant choisis parmi alkyle ou aryle ou des substituants voisins formant, avec les atomes de carbone du méthylène auxquels ils sont liés, un groupe phénylène substitué ou non; R2 et R3 représentent chacun hydrogène ou R2 et R3 répresentent ensemble une liaison; X représente O ou S; et n est égal à un nombre entier compris entre 2 et 6. L'invention décrit également un procédé de préparation de ce composé, une composition contenant ce composé et l'utilisation en médecine de ce composé ou de cette composition.
• [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents
  作者：Barrie C. C. Cantello、Michael A. Cawthorne、Graham P. Cottam、Peter T. Duff、David Haigh、Richard M. Hindley、Carolyn A. Lister、Stephen A. Smith、Peter L. Thurlby

  DOI：10.1021/jm00049a017

  日期：1994.11

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.