thiobenzoic acid S-(1-hydroxy-ethyl ester) | 109963-10-2

• 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: thiobenzoic acid S-(1-hydroxy-ethyl ester)
• 英文别名: Thiobenzoesaeure-S-(1-hydroxy-aethylester)；S-(1-hydroxyethyl) benzenecarbothioate
• CAS: 109963-10-2
• 化学式: C₉H₁₀O₂S
• 分子量: 182.243
• InChiKey: NKFXENZTYOKSQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙醛 、 硫代苯甲酸 生成 thiobenzoic acid S-(1-hydroxy-ethyl ester)
  参考文献：
  名称：

  Boehme et al., Justus Liebigs Annalen der Chemie, 1959, vol. 623, p. 92,96,102

  摘要：

  DOI：

文献信息

• Benzimidazole inhibitors of fructose 1,6-biphosphatase
  申请人：Metabasis Therapeutics, Inc.

  公开号：EP1402895A1

  公开（公告）日：2004-03-31

  Novel benzimidazole compounds of structure (1) and their use as fructose-1,6-bisphosphatase inhibitors is described wherein A, E, and L are selected from the group consisting of -NR82, -NO2, -H, -OR7, -SR7, -C(O)NR42, halo, -COR11, -SO2R3, guanidine, amidine, -NHSO2R5, -SO2NR42, -CN, sulfoxide, perhaloacyl, perhaloalkyl, perhaloakolxy, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, and lower alicyclic, or together A and L form a cyclic group, or together L and E form a cyclic group, or together E and J from a cyclic group including aryl, cyclic alkyl, and heterocyclic; J is selected from the group consiting -NR82, -NO2, -H, -OR7, -SR7, -C(O)NR42, halo, -C(O)R11, -CN, sulfonyl, sulfoxide, perhaloalkyl, hydroxyalkyl, perhaloalkoxy, alkyl, haloalkyl, aminoalkyl, alkenyl, alkynyl, alicyclic, aryl, and aralkyl, or together with Y forms a cyclic group including aryl, cyclic alkyl and heterocyclic alkyl; X is selected from the group consisting of alkylamino, alkyl(hydroxy), alkyl(carboxyl), alky(phosphonate), alkyl, alkenyl, alkynyl, alkyl(sulfonate), aryl, carbonylalkyl, 1,1-dihaloalkyl, aminocarbonylamino, alkylaminoalkyl, alkoxyalkyl, alkylthioalkyl, alkylthio, alkylaminocarbonyl, alkylcarbonylamino, alicyclic, aralkyl, and alkylaryl, all optionally substituted; or together with Y form a cyclic group including aryl, cyclic alkyl, and heterocyclic; Y is selected from the group consisting of -H, alkyl, alkenyl, alkynyl, aryl, alicyclic, aralkyl, aryloxyalkyl, alkoxyalkyl, -C(O)R3, -S(O)2,R3, -C(O)-R11, -CONHR3, -NR22, and-OR3, all except H are optionally substituted; or together with X form a cyclic group including aryl, cyclic alkyl, and heterocyclic; and pharmaceutically acceptable prodrugs and salts thereof.

  描述了结构(1)的新型苯并咪唑化合物及其作为果糖-1,6-二磷酸酶抑制剂的用途，其中A、E和L选自由-NR82、-NO2、-H、-OR7、-SR7、-C(O)NR42、卤素、-COR11、-SO2R3、胍、脒、-NHSO2R5、-SO2NR42、-CN、亚砜、全卤酰基、全卤烷基、全卤醇基、C1-C5 烷基、C2-C5 烯基、C2-C5 炔基和低级脂环族，或 A 和 L 共同组成一个环状基团，或 L 和 E 共同组成一个环状基团，或 E 和 J 共同组成一个包括芳基、环状烷基和杂环在内的环状基团；J选自由-NR82、- 、-H、-OR7、-SR7、-C(O)NR42、卤代、-C(O)R11、-CN、磺酰基、亚砜、全卤烷基、羟基烷基、全卤烷氧基、烷基、卤代烷基、氨基烷基、烯基、炔基、脂环基、芳基和芳烷基组成的基团，或与Y一起形成包括芳基、环烷基和杂环烷基在内的环状基团；X 选自烷基氨基、烷基（羟基）、烷基（羧基）、烷基（膦酸盐）、烷基、 烯基、炔基、烷基（磺酸盐）、芳基、羰基烷基、1,1-二卤代烷基、氨基羰基氨基、烷基氨基烷基、烷氧基烷基、烷硫基烷基、烷硫基、烷基氨基羰基、烷基羰基氨基、脂环族、芳基和烷芳基，均可选择被取代；或与 Y 一起形成环状基团，包括芳基、环烷基和杂环基；Y 选自-H、烷基、烯基、炔基、芳基、脂环族、芳烷基、芳氧基烷基、烷氧基烷基、-C(O)R3、-S(O)2,R3、-C(O)-R11、-CONHR3、-NR22 和-OR3 组成的组，除 H 外，所有均被任选取代；或与 X 一起形成一个环状基团，包括芳基、环烷基和杂环基；及其药学上可接受的原药和盐。
• NOVEL BENZIMIDAZOLE INHIBITORS OF FRUCTOSE-1,6-BISPHOSPHATASE
  申请人：Metabasis Therapeutics, Inc.

  公开号：EP0970095B1

  公开（公告）日：2003-10-29
• US6110903A
  申请人：——

  公开号：US6110903A

  公开（公告）日：2000-08-29
• US6399782B1
  申请人：——

  公开号：US6399782B1

  公开（公告）日：2002-06-04
• [EN] NOVEL BENZIMIDAZOLE INHIBITORS OF FRUCTOSE-1,6-BISPHOSPHATASE<br/>[FR] NOUVEAUX INHIBITEURS DE BENZIMIDAZOLE DE FRUCTOSE-1,6-BISPHOSPHATASE
  申请人：——

  公开号：WO1998039343A1

  公开（公告）日：1998-09-11

  [EN] Novel benzimidazole compounds of structure (1) and their use as fructose-1,6-bisphosphatase inhibitors is described wherein A, E, and L are selected from the group consisting of -NR<8>2, -NO2, -H, -OR<7>, -SR<7>, -C(O)NR<4>2, halo, -COR<11>, -SO2R<3>, guanidine, amidine, -NHSO2R<5>, -SO2NR<4>2, -CN, sulfoxide, perhaloacyl, perhaloalkyl, perhaloakolxy, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, and lower alicyclic, or together A and L form a cyclic group, or together L and E form a cyclic group, or together E and J form a cyclic group including aryl, cyclic alkyl, and heterocyclic; J is selected from the group consisting -NR<8>2, -NO2, -H, -OR<7>, -SR<7>, -C(O)NR<4>2, halo, -C(O)R<11>, -CN, sulfonyl, sulfoxide, perhaloalkyl, hydroxyalkyl, perhaloalkoxy, alkyl, haloalkyl, aminoalkyl, alkenyl, alkynyl, alicyclic, aryl, and aralkyl, or together with Y forms a cyclic group including aryl, cyclic alkyl and heterocyclic alkyl; X is selected from the group consisting of alkylamino, alkyl(hydroxy), alkyl(carboxyl), alkyl(phosphonate), alkyl, alkenyl, alkynyl, alkyl(sulfonate), aryl, carbonylalkyl, 1,1-dihaloalkyl, aminocarbonylamino, alkylaminoalkyl, alkoxyalkyl, alkylthioalkyl, alkylthio, alkylaminocarbonyl, alkylcarbonylamino, alicyclic, aralkyl, and alkylaryl, all optionally substituted; or together with Y form a cyclic group including aryl, cyclic alkyl, and heterocyclic; Y is selected from the group consisting of -H, alkyl, alkenyl, alkynyl, aryl, alicyclic, aralkyl, aryloxyalkyl, alkoxyalkyl, -C(O)R<3>, -S(O)2R<3>, -C(O)-R<11>, -CONHR<3>, -NR<2>2, and -OR<3>, all except H are optionally substituted; or together with X form a cyclic group including aryl, cyclic alkyl, and heterocyclic; and pharmaceutically acceptable prodrugs and salts thereof.
  [FR] L'invention concerne de nouveaux composés de benzimidazole de structure (1), ainsi que leur utilisation en tant qu'inhibiteurs de fructose-1,6-bisphosphatase: dans laquelle: A, E et L sont choisis dans le groupe composé de -NR<8>2, -NO2, -H, -OR<7>, -SR<7>, -C(O)NR<4>2, halo, -COR<11>, -SO2R<3>, guanidine, amidine, -NHSO2R<5>, -SO2NR<4>2, -CN, sulfoxyde, perhaloacyle, perhaloalkyle, perhaloalkoxy, alkyle en C1-C5, alkényle en C2-C5, alkynyle en C2-C5, et alicyclique inférieur; ou A et L forment un groupe cyclique, ou L et E forment un groupe cyclique, ou E et J forment un groupe cyclique renfermant aryle, alkyle cyclique, et hétérocyclique; J est choisi dans le groupe composé de -NR<8>2, -NO2, -H, -OR<7>, -SR<7>, -C(O)NR<4>2, halo, -C(O)R<11>, -CN, sulfuryle, sulfoxyde, perhaloalkyle, hydroxyalkyle, perhaloalkoxy, alkyle, haloalkyle, aminoalkyle, alkényle, alkynyle, alicyclique, aryle, et aralkyle, ou forme avec Y un groupe cyclique renfermant aryle, alkyle cyclique et alkyle hétérocyclique; X est choisi dans le groupe composé de alkylamino, alkylehydroxy), alkyle(carboxyle), alkyle(phosphonate), alkyle, alkényle, alkynyle, alkyle(sulfonate), aryle, carbonylalkyle, 1,1-dihaloalkyle, aminocarbonylamino, alkylaminoalkyle, alkoxyalkyle, alkylthioalkyle, alkylthio, alkylaminocarbonyle, alkylcarbonylamino, alicyclique, aralkyle, et alkylaryle, tous éventuellement substitués, ou forme avec Y un groupe cyclique renfermant aryle, alkyle cyclique, et hétérocyclique; Y est choisi dans le groupe composé de -H, alkyle, alkényle, alkynyle, aryle, alicyclique, aralkyle, aryloxyalkyle, alkoxyalkyle, -C(O)R<3>, -S(O)2R<3>, -C(O)R<11>, -CONHR<3>, -NR<2>2, et -OR<3>, tous sauf H étant éventuellement substitués, ou forme avec X un groupe cyclique renfermant aryle, alkyle cyclique, et hétérocyclique. L'invention concerne également les promédicaments pharmaceutiquement acceptables et les sels de ces composés.