5-methyl-2H-1,4-thiazin-3(4H)-one | 22390-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: 5-methyl-2H-1,4-thiazin-3(4H)-one
• 英文别名: 5-methyl-4H-1,4-thiazin-3-one
• CAS: 22390-69-8
• 化学式: C₅H₇NOS
• mdl: MFCD00507009
• 分子量: 129.183
• InChiKey: GYYVFGWKPDSNLK-UHFFFAOYSA-N

物化性质

• 沸点：
  335.0±35.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-2H-1,4-thiazin-3(4H)-one 在 间氯过氧苯甲酸 作用下， 以 丙酮 为溶剂， 反应 0.25h， 以80%的产率得到5-methyl-2H-1,4-thiazin-3(4H)-one 1-sulfoxide
  参考文献：
  名称：

  Synthesis of 3-Substituted 2-Oxo-1,4-thiazines and Evaluation of Their Protective Effect against Endotoxin Shock in Mouse.

  摘要：

  5-甲基-2, 3-二氧基-2H, 4H-1, 4-噻唑啉（7）是通过用m-氯过苯甲酸在甲醇中氧化5-甲基-2H-1, 4-噻唑-3(4H)-酮（5），然后对所得的2, 2-二甲氧基-1, 4-噻唑啉（6）进行酸水解得到的。3-氯-2-氧基-1, 4-噻唑啉（10）是通过将7与氧氯化磷加热反应得到的，它与多种亲核试剂发生反应生成3-取代的2-氧基-1, 4-噻唑啉（11a-y）。其中一些2-氧基-1, 4-噻唑啉，11a-b、e、o和r-s，表现出对D-半乳糖胺敏感小鼠的内毒素休克具有保护作用。

  DOI：

  10.1248/cpb.40.1025
• 作为产物：
  描述：

  2-巯基乙胺 、 一氯丙酮 生成 5-methyl-2H-1,4-thiazin-3(4H)-one
  参考文献：
  名称：

  巯基乙醇酰胺与卤代甲基酮的反应。

  摘要：

  DOI：

  10.1021/ja01190a512

文献信息

• Studies on bi-heterocyclic compounds. I. 6-Substituted dihydro-1,4-thiazinones.
  作者：HIROAKI YAMAZAKI、HIDENORI HARADA、KENICHI MATSUZAKI、KIMITOMO YOSHIOKA、MUNEAKI TAKASE、EIJI OHKI

  DOI：10.1248/cpb.35.2243

  日期：——

  Reactions of 5-methyl-2H-1, 4-thiazin-3 (4H) -one (4) with various N-acylpyridinium salts (7a-g) led to (N-acyldihydropyridyl) thiazinones (5a-g), oxidation of which yielded a new class of pyridylthiazinones (6a-g). These reactions were applied to the synthesis of other azaarylthiazinones. Some of these azaarylthiazinones, particularly 6- (4-pyridyl) thiazinones (6a, 14a and 14b) showed positive inotropic activity with little chronotropic effect on guinea pig left atria.

  5-甲基-2H-1,4-噻嗪-3(4H)-酮(4)与各种N-酰基吡啶盐(7a-g)反应得到(N-酰基二氢吡啶基)噻嗪酮(5a-g)，将其氧化得到一类新的吡啶基噻嗪酮(6a-g)。这些反应被应用于其他含氮芳基噻嗪酮的合成。其中一些含氮芳基噻嗪酮，特别是6-(4-吡啶基)噻嗪酮(6a, 14a和14b)，显示出了对豚鼠左心房有正性肌力作用和较小的变时效应。
• Thiazole derivatives and medical compositions thereof
  申请人：Zenyaku Kogyo Kabushiki Kaisha

  公开号：US04804668A1

  公开（公告）日：1989-02-14

  A thiazole derivative represented by the formula I, pharmaceutically acceptable acid addition salt thereof, and a process for preparation thereof ##STR1## wherein R.sub.1 represents --COOR.sub.4, ##STR2## or cyano wherein R.sub.4 represents hydrogen or lower alkyl, and R.sub.5 and R.sub.6 may be the same or different and represent hydrogen, lower alkyl, aryl, amino-lower alkyl, N-lower alkylamino-lower alkyl, N,N-di-lower alkylamino-lower alkyl or R.sub.5 and R.sub.6 are joined to form a N-containing heterocyclic group; R.sub.2 represents hydrogen or lower alkyl; and R.sub.3 represents N-containing heterocyclic group. These compounds are useful as cardiotonic agents.

  一种由式I表示的噻唑衍生物，其药学上可接受的酸盐，以及其制备方法。其中，R₁代表--COOR₄，R₂代表氢或较低烷基，R₃代表含氮的杂环基团。这些化合物可用作强心剂。
• 1,4-thiazine derivative, and cardiotonic agent comprising it as
  申请人：Zenyaku Kogyo Kabushiki Kaisha

  公开号：US04800201A1

  公开（公告）日：1989-01-24

  A novel 1,4-thiazine derivative represented by the formula I, a pharmaceutically acceptable acid addition salt thereof, a process for preparation thereof and a cardiotonic agent comprising it as an effective component; ##STR1## wherein R.sub.1 and R.sub.2 represent respectively hydrogen atom, lower alkyl group, lower alkoxy group, amino group, lower alkyl-amino group, aryl-amino group, hydroxy group, aryl group or 5- or 6-membered heterocyclic residue; R.sub.3 and R.sub.4 represent hydrogen atom or lower alkyl group; and R.sub.5 represents N-containing heterocyclic residue and is not pyridinyl group when R.sub.1 and R.sub.2 represent hydrogen atom and R.sub.3 and R.sub.4 represent hydrogen atom or lower alkyl group.

  一种由式I代表的新型1,4-噻嗪衍生物，其药学上可接受的酸盐，其制备方法以及作为有效成分的强心药剂；其中R.sub.1和R.sub.2分别代表氢原子，较低的烷基基团，较低的烷氧基团，氨基，较低的烷基氨基团，芳基氨基团，羟基，芳基或5-或6-成员杂环残基；R.sub.3和R.sub.4代表氢原子或较低的烷基基团；R.sub.5代表含氮杂环残基，当R.sub.1和R.sub.2代表氢原子且R.sub.3和R.sub.4代表氢原子或较低的烷基基团时，R.sub.5不代表吡啶基。
• 1,4-Thiazine derivatives
  申请人：Zenyaku Kogyo Kabushiki Kaisha

  公开号：US04565813A1

  公开（公告）日：1986-01-21

  Disclosed is a novel 1,4-thiazine derivatives represented by the following general formula I and a pharmaceutically acceptable acid addition salt thereof: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 respectively represent a hydrogen atom or a lower alkyl group. Also disclosed are processes for preparation of a novel thiazine derivative represented by the general formula I, which comprise reacting a compound of the general formula III with a compound of the general formula A-X' in a compound containing a pyridinyl group as a solvent to obtain a compound of the general formula II: ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above, A represents a group ##STR3## in which X represents a halogen atom and n is a number of 1 to 3, and X' represents a halogen atom which may be the same as or different from X, and reacting the compound of the general formula II with sulfur at elevated temperature or stirring the compound of the general formula II in a solution system comprising zinc and a carboxylic acid. Further disclosed is a cardiotonic agent comprising a pharmaceutically acceptable excipient and, as the active component thereof, an effective amount of the novel 1,4-thiazine derivative having the general formula I.

  本发明公开了一种由以下一般式I表示的新颖的1,4-噻嗪衍生物及其药学上可接受的酸盐：其中R.sub.1、R.sub.2和R.sub.3分别表示氢原子或较低的烷基基团。还公开了制备由一般式I表示的新颖噻嗪衍生物的方法，包括将一般式III的化合物与一般式A-X'的化合物在含有吡啶基团的化合物中作为溶剂中反应，以获得一般式II的化合物：其中R.sub.1、R.sub.2和R.sub.3如上所定义，A代表一个基团##在其中X代表卤原子，n为1至3的数，X'代表可能与X相同或不同的卤原子，并且将一般式II的化合物与硫在高温下反应或将一般式II的化合物在包含锌和羧酸的溶液体系中搅拌。还公开了一种包括药学上可接受的赋形剂和作为其活性成分的一种有效量的具有一般式I的新颖1,4-噻嗪衍生物的强心剂。
• Cyclic amidine inhibitors of indolamine N-methyltransferase
  作者：Joshua Rokach、Pierre Hamel、Norman R. Hunter、Grant Reader、Clarence S. Rooney、Paul S. Anderson、Edward J. Cragoe、Lewis R. Mandel

  DOI：10.1021/jm00189a004

  日期：1979.3

  Syntheses of a large number of mono- and bicyclic, as well as a few tricyclic, amidine derivatives related to 2,3,4,6,7,8,-hexahydropyrrolo[1,2-a]pyrimidine (DBN) are reported. In vitro potencies for inhibition of the enzyme indolamine N-methyltransferase (INMT) from rabbit and human lung are presented. Four bicyclic amidine derivatives and 11 monocyclic derivatives were found to be equal or superior to DBN in in vitro potencies. With the bicyclic amidines, increasing ring size or introduction of substituents reduced activity. Among the monocyclic analogues, the most potent representatives were five- or six-membered systems with an exocyclic imino group, combined with methyl of ethyl substituents on the endocyclic nitrogen. Introduction of additonal substituents decreased inhibitory potency. 2,3,5,6-Tetrahydro-8H-imidazo[2,1-c][1,4]thiazine and 3-methyl-2-iminothiazolidine have been shown to cause inhibition of lung INMT when administered orally to rabbits.