(S)-3'-(CH3O)-DADFT | 847355-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-3'-(CH3O)-DADFT
• 英文别名: (4S)-2-(2-hydroxy-3-methoxyphenyl)-4-methyl-5H-1,3-thiazole-4-carboxylic acid
• CAS: 847355-89-9
• 化学式: C₁₂H₁₃NO₄S
• 分子量: 267.306
• InChiKey: AZITWJOFVGSTQA-GFCCVEGCSA-N

物化性质

• 熔点：
  158-160 °C
• 沸点：
  476.3±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sodium hydroxide 、 (S)-3'-(CH3O)-DADFT 以 H₂₀ 为溶剂， 生成 sodium;(4S)-2-(2-hydroxy-3-methoxyphenyl)-4-methyl-5H-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  WO2008/115433

  摘要：

  公开号：
• 作为产物：
  描述：

  2-羟基-3-甲氧基苯甲腈 、 2-甲基-D-半胱氨酸盐酸盐 在 phosphate buffer 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以39%的产率得到(S)-3'-(CH3O)-DADFT
  参考文献：
  名称：

  Partition-Variant Desferrithiocin Analogues:  Organ Targeting and Increased Iron Clearance

  摘要：

  Altering the lipophilicity (log P-app) of desferrithiocin analogues can change the organ distribution of the chelators and lead to enhanced iron clearance. For example, alkylation of (S)-2-(2,4-dihydroxyphenyl)-4,5-dihydro-4-methyl-4-thiazolecarboxylic acid [(S)-4'-(HO)-DADFT] and its analogues to more lipophilic compounds, such as (S)-4,5-dihydro-2-(2-hydroxy-4-methoxyphenyl)4-methyl-4-thiazolecarboxylic acid [(S)-4'-(CH3O)-DADFT], provides ligands that achieved between a 3- and 8-fold increase in chelator concentrations in the heart, liver, and pancreas (the organs most at risk in iron-overload disease) of treated rodents. The 4'-O-methylated compounds are demethylated to their hydroxylated counterparts in rodents; furthermore, this O-demethylation takes place in both rodent and human liver microsomes. The relationship between chelator lipophilicity and iron-clearing efficacy in the iron-overloaded Cebus apella primate is further underscored by a comparison of the iron-clearing efficiency of (S)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-4-methyl-4-thiazolecarboxylic acid [(S)-3'-(HO)-DADFT] and its 3'-(CH3O) counterpart. Finally, these DFT analogues are shown to be both inhibitors of the iron-mediated oxidation of ascorbate as well as effective radical scavengers.

  DOI：

  10.1021/jm049306x

文献信息

• Process for the preparation of substituted thiazolines and their intermediates
  申请人：——

  公开号：US20030088105A1

  公开（公告）日：2003-05-08

  Process for the preparation of substituted thiazolines of the formula (I) 1 in which Ar is a phenyl, naphthyl, thienyl, pyridyl or quinolinyl radical which can optionally be substituted by one or more substituents from the group consisting of halogen, OH, benzyloxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, COOR 1 where R 1 is H or C 1 -C 4 -alkyl, by coupling of (S)-&agr;-methylcysteine hydrochloride of the formula (II) 2 with a nitrile of the formula (III) Ar—CN in which Ar is as defined above, or a corresponding C 1 -C 4 -alkyl imidate, in which (S)-a-methylcysteine hydrochloride of the formula (II) is reacted in a suitable solvent with a nitrile of the formula (III) or a corresponding C 1 -C 4 -alkyl imidate in the presence of a tertiary base at a pH of 6.5 to 10 at 50° C. up to the reflux temperature to give the corresponding thiazoline of the formula (I), and processes for the preparation of (S)-&agr;-methylcysteine hydrochloride and its use for the preparation of thiazolines of the formula (I).

  制备式(I)的取代噻唑环的过程，其中Ar是苯基、萘基、噻吩基、吡啶基或喹啉基，可以选择性地由卤素、OH、苄氧基、C1-C4烷基、C1-C4烷氧基、COOR1（其中R1为H或C1-C4烷基）中的一个或多个取代基取代，通过(S)-α-甲基半胱氨酸盐酸盐的配对反应，配对反应的反应物为式(II)2和式(III)Ar—CN的腈或相应的C1-C4烷基亚胺，其中(S)-α-甲基半胱氨酸盐酸盐的配对反应物式(II)在适当的溶剂中与式(III)的腈或相应的C1-C4烷基亚胺在三级碱存在下，在pH为6.5至10、50℃至回流温度下反应，得到相应的式(I)的噻唑环，以及制备(S)-α-甲基半胱氨酸盐酸盐的过程及其用于制备式(I)的噻唑环的方法。
• DESFERRITHIOCIN POLYETHER ANALOGUES
  申请人：Bergeron, JR. Raymond J.

  公开号：US20100093812A1

  公开（公告）日：2010-04-15

  A relatively non-toxic desazadesferrithiocin analog having the formula (I): wherein: R 1 , R 2 , R 4 and R 5 may be the same or different and may be H, straight or branched chain alkyl having up to 14 carbon atoms, e.g., methyl, ethyl, propyl and butyl, or arylalkyl wherein the aryl portion is hydrocarbyl and the alkyl portion is straight or branched chain, the arylalkyl group having up to 14 carbon atoms, R2 optionally being alkoxy having up to 14 carbon atoms; R 3 is [(CH 2 ) n —O] x —[(CH 2 ) n —O] y -alkyl; n is, independently, an integer from 1 to 8; x is an integer from 1 to 8; y is an integer from O to 8, and R 3 O may occupy any position on the phenyl ring except the 4-position, or a salt, hydrate or solvate thereof; and methods and compositions for treating the effects of trivalent metal, i.e., iron, overload.

  一种相对无毒的去除铁过载的治疗方法，使用化学式（I）的类去铁血红素衍生物，其中：R1、R2、R4和R5可以相同或不同，可以是氢，直链或支链烷基，碳数不超过14个，例如，甲基，乙基，丙基和丁基，或芳基烷基，其中芳基部分为烃基，烷基部分为直链或支链，芳基烷基的碳数不超过14个，R2可以选择为碳数不超过14个的烷氧基；R3为[(CH2)n-O]x-[(CH2)n-O]y-烷基；n独立地为1到8的整数；x为1到8的整数；y为0到8的整数，R3O可以占据苯环上除4位以外的任何位置，或其盐，水合物或溶剂化物；以及治疗三价金属，即铁，过载的方法和组合物。
• US6894170B2
  申请人：——

  公开号：US6894170B2

  公开（公告）日：2005-05-17
• US8324397B2
  申请人：——

  公开号：US8324397B2

  公开（公告）日：2012-12-04
• US9174948B2
  申请人：——

  公开号：US9174948B2

  公开（公告）日：2015-11-03