2-tert-butyl-1,3-thiazolidin-3-ium-4-carboxylate

• 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: 2-tert-butyl-1,3-thiazolidin-3-ium-4-carboxylate
• 化学式: C8H15NO2S
• 分子量: 189.28
• InChiKey: XCEINABKQJDSRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

文献信息

• Method for producing chiral mercapto amino acids
  申请人：Kotthaus Martina

  公开号：US20070112216A1

  公开（公告）日：2007-05-17

  The invention relates to a method for producing chiral mercapto amino acids of formula (I) wherein R 1 , R 2 and R 3 can represent hydrogen, C 6 -C 12 aryl, C 1 -C 6 -alkyl-C 6 -C 12 -aryl, C 6 -C 12 -aryl-C 1 -C 6 -alkyl, C 1 -C 18 -alkyl or C 2 -C 18 -alkenyl, R 2 and R 3 forming a saturated or unsaturated ring. According to said method, a) an oxo compound of formula (II), wherein X represents a leaving group, is reacted in the presence of ammonia or ammonium hydroxide and a sulfide, optionally under phase transfer catalysis or addition of a solubiliser, with a ketone or an aldehyde of formula (III) wherein R 4 and R 5 can represent a C 1 -C 12 alkyl radical or a C 6 -C 20 aryl radical or one of the two radicals H, or R 4 and R 5 together form a C 4 -C 7 ring, to form the compound of formula (IV), that b) reacts with HCN to form the corresponding nitrile, whereupon c) the crystallised nitrile is converted, by selective hydrolysis by means of a mineral acid, into the corresponding amide of formula (VI), and d) is then converted into the corresponding chiral amide of formula (VI*) by means of an L amidase or a chiral dissociating acid, whereupon by reaction with an acid, the desired chiral mercapto amino acid of formula (I) is obtained, or e) first the reaction with an acid is carried out, and then the conversion into the chiral mercapto amino acid takes place.

  该发明涉及一种生产手性巯基氨基酸的方法，其化学式为(I)，其中R1、R2和R3可以代表氢、C6-C12芳基、C1-C6烷基-C6-C12芳基、C6-C12芳基-C1-C6烷基、C1-C18烷基或C2-C18烯基，R2和R3形成饱和或不饱和环。根据该方法，a）在氨或氢氧化铵存在下，将具有化学式(II)的羰基化合物，其中X代表离去基团，与具有化学式(III)的酮或醛反应，其中R4和R5可以代表C1-C12烷基基团或C6-C20芳基基团或两个基团H中的一个，或者R4和R5一起形成C4-C7环，形成具有化学式(IV)的化合物，然后b）与HCN反应形成相应的腈，随后c）通过矿酸的选择性水解将结晶的腈转化为具有化学式(VI)的相应酰胺，并且d）通过L-酰胺酶或手性分离酸将其转化为具有化学式(VI*)的相应手性酰胺，然后通过与酸的反应得到所需的手性巯基氨基酸，或者e）首先进行与酸的反应，然后进行转化为手性巯基氨基酸。
• 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。
• Heterocyclic metalloprotease inhibitors
  申请人：The Procter & Gamble Company

  公开号：US20030186958A1

  公开（公告）日：2003-10-02

  The invention provides compounds of formula 1 as described in the claims, or an optical isomer, diastereomer or enantiomer thereof, or a pharmaceutically-acceptable salt, or biohydrolyzable amide, ester, or imide thereof are useful as inhibitors of metalloproteases. Also disclosed are pharmaceutical compositions and methods of treating diseases, disorders and conditions characterized by metalloprotease activity using these compounds or the pharmaceutical compositions containing them.

  本发明提供了式 1 的化合物 1 或其光学异构体、非对映异构体或对映体，或其药学上可接受的盐，或其生物可水解的酰胺、酯或亚胺，可作为金属蛋白酶的抑制剂。 此外，还公开了使用这些化合物或含有这些化合物的药物组合物治疗以金属蛋白酶活性为特征的疾病、失调和病症的药物组合物和方法。
• HETEROCYCLIC METALLOPROTEASE INHIBITORS
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0925287B1

  公开（公告）日：2003-01-15
• METHODS FOR TREATING INFLAMMATORY DISEASE BY ADMINISTERING ALDEHYDES AND DERIVATIVES THEREOF
  申请人：ALFAMA - INVESTIGAÇÃO E DESENVOLVIMENTO DE PRODUTO

  公开号：EP2099439A2

  公开（公告）日：2009-09-16