3,4-二乙氧基苯-1-甲硫代酰胺 | 60759-00-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3,4-二乙氧基苯-1-甲硫代酰胺
• 英文名称: 3,4-diethoxybenzthioamide
• 英文别名: 3,4-diethoxythiobenzamide；3,4-Diethoxybenzothioamide；3,4-diethoxybenzenecarbothioamide
• CAS: 60759-00-4
• 化学式: C₁₁H₁₅NO₂S
• mdl: MFCD08164124
• 分子量: 225.312
• InChiKey: CCDWRZYGBRUZLU-UHFFFAOYSA-N

物化性质

• 沸点：
  348.4±52.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  76.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二乙氧基苯-1-甲硫代酰胺 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 2-[2-(3,4-Diethoxyphenyl)-1,3-thiazol-4-yl]benzoic acid
  参考文献：
  名称：

  Novel Thiazole Derivatives as Inhibitors of Superoxide Production by Human Neutrophils: Synthesis and Structure-Activity Relationships

  摘要：

  Neutrophils have an important role in the self-defense systems of organisms through the production of superoxide. On the other hand, it has been proposed that abnormal amounts of superoxide produced by neutrophils are a serious factor in tissue injury. A series of novel thiazole derivatives was prepared and evaluated inhibitory effect on superoxide production by human neutrophils in vitro. Among these compounds, 6-[2-(3,4-diethoxyphenyl)thiazol-4-yl]-pyridine-2-carboxylic acid (OPC-6535) was selected as one of the most promising compounds. The synthesis and structure-activity relationships of these compounds are reported herein.

  DOI：

  10.1021/jm00002a017
• 作为产物：
  描述：

  3,4-二乙氧基苯甲腈 在 盐酸 、 硫代乙酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以74.5%的产率得到3,4-二乙氧基苯-1-甲硫代酰胺
  参考文献：
  名称：

  Novel Thiazole Derivatives as Inhibitors of Superoxide Production by Human Neutrophils: Synthesis and Structure-Activity Relationships

  摘要：

  Neutrophils have an important role in the self-defense systems of organisms through the production of superoxide. On the other hand, it has been proposed that abnormal amounts of superoxide produced by neutrophils are a serious factor in tissue injury. A series of novel thiazole derivatives was prepared and evaluated inhibitory effect on superoxide production by human neutrophils in vitro. Among these compounds, 6-[2-(3,4-diethoxyphenyl)thiazol-4-yl]-pyridine-2-carboxylic acid (OPC-6535) was selected as one of the most promising compounds. The synthesis and structure-activity relationships of these compounds are reported herein.

  DOI：

  10.1021/jm00002a017
• 作为试剂：
  描述：

  3,4-二乙氧基苯-1-甲硫代酰胺 、 6-(2-溴乙酰基)吡啶甲酸 在 3,4-二乙氧基苯-1-甲硫代酰胺 作用下， 以71的产率得到methyl 6-<2-(3,4-diethoxyphenyl)thiazol-4-yl>pyridine-2-carboxylate
  参考文献：
  名称：

  J. Med. Chem. 1995, 38, 353-358

  摘要：

  DOI：

文献信息

• Thiazole derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05639770A1

  公开（公告）日：1997-06-17

  A thiazole derivative of the general formula: ##STR1## The thiazole derivatives have an excellent inhibitory activity for superoxide radical.

  一种通式为##STR1##的噻唑衍生物。这些噻唑衍生物对超氧自由基具有出色的抑制活性。
• Agent for inhibition of cytokine production and agent for inhibition of cell adhesion
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US06291487B1

  公开（公告）日：2001-09-18

  The present invention provides an agent for inhibiting cytokine production or cell adhesion, comprising at least one compound selected from the group consisting of thiazole derivatives represented by the following general formula: [wherein R1 is a phenyl group which may have a lower alkoxy group(s) as a substituent(s) on the phenyl ring, and R2 is a group represented by the following general formula: [wherein R3's, which may be the same or different, are each a carboxyl group, a lower alkoxy group or the like) or the like] and salts thereof.

  本发明提供了一种用于抑制细胞因子产生或细胞粘附的药剂，包括至少一种选择自以下一般式所代表的噻唑衍生物组合的化合物： [其中R1是苯基，苯环上可能有一个或多个较低的烷氧基作为取代基，R2是由以下一般式所代表的基团： [其中R3可能相同也可能不同，每个都是羧基、较低的烷氧基或类似物）或其盐。
• THIAZOLE COMPOUND AND USE THEREOF
  申请人：Otsuka Pharmaceutical Company, Limited

  公开号：EP1748044A1

  公开（公告）日：2007-01-31

  An object of the present invention is to provide a novel thiazole compound with specific inhibitory activity against phosphodiesterase 4. The present invention provides a compound represented by Formula (1), an optical isomer thereof, or a salt thereof: wherein R1 is a di-C1-6 alkoxyphenyl group; R2 is any one of the following groups (a) to (t): (a) a phenyl group; (b) a naphthyl group; (c) a pyridyl group; (d) a furyl group; (e) a thienyl group; (f) an isoxazolyl group; (g) a thiazolyl group; (h) a pyrrolyl group; (i) an imidazolyl group; (j) a tetrazolyl group; (k) a pyrazinyl group; (1) a thienothienyl group; (m) a benzothienyl group; (n) an indolyl group; (o) a benzimidazolyl group; (p) an indazolyl group; (q) a quinolyl group; (r) a 1,2,3,4-tetrahydroquinolyl group; (s) a quinoxalinyl group; and (t) a 1,3-benzodioxolyl group; and A is any one of the following groups (i) to (vi): (i) -CO-B- wherein B is a C1-6 alkylene group; (ii) -CO-Ba wherein Ba is a C2-6 alkenylene group; (iii) -CH(OH)-B-; (iv) -COCH(COOR3)-Bb- wherein R3 is a C1-6 alkyl group and Bb is a C1-6 alkylene group; and (v) -Bc- wherein Bc is a C2-6 alkylene group.

  本发明的目的是提供一种对磷酸二酯酶4具有特异抑制活性的新型噻唑化合物。本发明提供一种由式（1）表示的化合物，其光学异构体或盐：其中R1是二C1-6烷氧基苯基基团；R2是以下分组之一（a）至（t）中的任意一种：（a）苯基；（b）萘基；（c）吡啶基；（d）呋喃基；（e）噻吩基；（f）异氧唑基；（g）噻唑基；（h）吡咯基；（i）咪唑基；（j）四唑基；（k）吡嗪基；（l）噻吩噻吩基；（m）苯并噻吩基；（n）吲哚基；（o）苯并咪唑基；（p）吲哚基；（q）喹啉基；（r）1,2,3,4-四氢喹啉基；（s）喹啉基；和（t）1,3-苯并二氧杂环戊基；以及A是以下分组之一（i）至（vi）中的任意一种：（i）-CO-B-，其中B是C1-6烷基基团；（ii）-CO-Ba，其中Ba是C2-6烯基基团；（iii）-CH(OH)-B-；（iv）-COCH(COOR3)-Bb-，其中R3是C1-6烷基基团，Bb是C1-6烷基基团；和（v）-Bc-，其中Bc是C2-6烷基基团。
• [EN] AGENT FOR INHIBITION OF CYTOKINE PRODUCTION AND AGENT FOR INHIBITION OF CELL ADHESION<br/>[FR] AGENT INHIBANT LA PRODUCTION DE CYTOKINE ET AGENT INHIBANT L'ADHESION CELLULAIRE
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：WO1998014191A1

  公开（公告）日：1998-04-09

  (EN) The present invention provides an agent for inhibiting cytokine production or cell adhesion, comprising at least one compound selected from the group consisting of thiazole derivatives represented by general formula (1), wherein R1 is a phenyl group which may have a lower alkoxy group(s) as a substituent(s) on the phenyl ring, and R2 is a group represented by general formula (2), wherein R3s, which may be the same or different, are each a carboxyl group, a lower alkoxy group or the like, and salts thereof.(FR) Cette invention se rapporte à une agent inhibant la production de cytokine ou l'adhésion cellulaire qui comprend au moins un composé choisi dans le groupe constitué par des dérivés de thiazole représentés par la formule générale (1) où R1 représente un groupe phényle pouvant comportant un ou plusieurs groupes alcoxy inférieur comme substituant(s) sur le cycle phényle; et R2 représente un groupe représenté par la formule générale (2) où les éléments R3, qui peuvent être identiques ou différents, représentent chacun un groupe carboxyle, un groupe alcoxy inférieur ou similaire, cette invention se rapportant également à des sels d'un tel composé.

  本发明提供一种抑制细胞因子产生或细胞黏附的药剂，包括至少一种选择自通式（1）所表示的噻唑衍生物，其中R1是苯基，可能在苯环上具有一个或多个较低的烷氧基作为取代基，而R2是由通式（2）所表示的基团，其中R3s可能相同或不同，每个都是羧基、较低的烷氧基或类似物，以及其盐。
• Superoxide radical inhibitor
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05643932A1

  公开（公告）日：1997-07-01

  A superoxide radical inhibitor containing, as an effective ingredient, an azole derivative represented by the general formula (1), ##STR1## [wherein R.sup.1 represents a phenyl group which may have 1-3 lower alkoxy groups as substituent(s) on the phenyl ring, a phenyl group having a lower alkylenedioxy group, or the like; R.sup.2 represents a hydrogen atom, a phenyl group, a halogen atom, a lower alkoxycarbonyl group, a lower alkyl group, an amino-lower alkyl group which may have a lower alkyl group as a substituent, a dihydrocarbostyril group, or the like; R.sup.3 represents a group of the formula, ##STR2## (R.sup.4B represents a hydroxyl group, a carboxy group, a lower alkenyl group or a lower alkyl group. m represents 0, 1 or 2); X represents a sulfur atom or an oxygen atom] or a salt thereof.

  一种超氧自由基抑制剂，其有效成分为一种由通式（1）表示的唑类衍生物，##STR1## [其中R.sup.1代表苯基，该苯基上可能有1-3个低烷氧基作为取代基，苯基带有低烷基二氧基基团或类似基团；R.sup.2代表氢原子，苯基，卤素原子，低烷氧羰基基团，低烷基，氨基-低烷基基团，该基团可能带有低烷基取代基，二氢草酰基基团或类似基团；R.sup.3代表式的基团，##STR2## （其中R.sup.4B代表羟基，羧基，低烯基基团或低烷基基团。m代表0、1或2）；X代表硫原子或氧原子]或其盐。