3,4-dihydro-3-oxo-2H-[1,4]thiazin | 37128-08-8

• 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: 3,4-dihydro-3-oxo-2H-[1,4]thiazin
• 英文别名: 2H-1,4-Thiazin-3(4H)-one；1,4-thiazine-3-one；2,3-Dihydro-4H-1,4-thiazin-3-one；1,4-thiazin-3(4H)-one；4H-[1,4]thiazin-3-one；4H-1,4-thiazin-3-one
• CAS: 37128-08-8
• 化学式: C₄H₅NOS
• mdl: MFCD01111761
• 分子量: 115.156
• InChiKey: UIRSLBDCOYTZPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  3,4-dihydro-3-oxo-2H-[1,4]thiazin 在 间氯过氧苯甲酸 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以90.5%的产率得到2H-1,4-Thiazin-3(4H)-one 1-Oxide
  参考文献：
  名称：

  尿嘧啶的结构类似物2 H -1,4-thiazin-3（4 H）-one 1-oxide和2 H -1,4-thiazin-3-（4 H）-one 1,1-dioxide的合成

  摘要：

  描述了抗生素阿米霉素的1,4-噻嗪1-氧化物和1,1-二氧化物类似物的合成。甲基硫代乙醇酸酯与1-溴-2,2-二乙氧基乙烷的反应，得到（2,2-二乙氧基乙基硫基）乙酸甲酯（2）。用甲醇氨处理2，然后环化，得到2 H -1，4-噻嗪-3（4 H）-一（5）。氧化5与米氯过氧酸转换它为2 ħ -1,4-噻嗪-3（4 H ^） -酮1-氧化物（6）。用高锰酸钾氧化2，然后用甲醇氨处理，环化得到2 H-1,4-噻嗪-3（4 H）-1,1-二氧化物。

  DOI：

  10.1002/jhet.5570190125
• 作为产物：
  描述：

  2-(2',2'-Diethoxyethylthio)acetamide 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以92%的产率得到3,4-dihydro-3-oxo-2H-[1,4]thiazin
  参考文献：
  名称：

  橄榄酸类似物的合成。含3-（2-乙酰氨基乙硫基）侧链的7-氧代-1-氮杂双环[3.2.0]庚-2-烯-2-羧酸酯的制备

  摘要：

  由4-羧甲基氮杂环丁烷-2-酮制备2-乙酰氨基乙烯基硫代酸酯，并通过分子内Wittig反应环化以提供3-（2-乙酰氨基乙烯基硫代）-7-氧代-1-氮杂双环[3.2.0]庚-2-烯-2 -羧酸盐，与天然存在的抗生素MM 13902（1）密切相关的类似物。

  DOI：

  10.1039/c39800000429

文献信息

• Thiazine or thiomorpholine derivatives
  申请人：Santen Pharmaceutical Co., Ltd.

  公开号：US05556841A1

  公开（公告）日：1996-09-17

  This invention relates to the compounds of the formula [I] which are useful for the treatment of cataracts, and the synthetic intermediates of the formula [II], ##STR1## wherein R.sup.1 is hydroxy which can be protected by a hydroxy protective group; R.sup.2 is lower alkyl; R.sup.3 is hydrogen, lower alkyl, hydroxy, which can be protected by a hydroxy protective group, or lower alkoxy, and the said lower alkyl can be substituted by hydroxy, which can be protected by a hydroxy protective group, amino or lower alkylamino; R.sup.4 is carboxy which can be converted into ester or amide; tetrazolyl; phosphono which can be converted into ester or amide; or sulfonyl which can be converted into ester or amide; R.sup.5 is cyano or lower alkoxy; A is alkylene; B is C.dbd.O, C.dbd.S or CH.sub.2, and is single bond or double bond.

  这项发明涉及具有以下式[I]的化合物，这些化合物对白内障的治疗有用，并且具有以下式[II]的合成中间体，其中R.sup.1是可以通过羟基保护基保护的羟基；R.sup.2是较低的烷基；R.sup.3是氢、较低的烷基、羟基（可以通过羟基保护基保护）、或较低的烷氧基，所述较低的烷基可以被羟基（可以通过羟基保护基保护）、氨基或较低的烷基氨基取代；R.sup.4是可以转化为酯或酰胺的羧基；四唑基；可以转化为酯或酰胺的膦酸基；或可以转化为酯或酰胺的磺酰基；R.sup.5是氰基或较低的烷氧基；A是烷基；B是C.dbd.O、C.dbd.S或CH.sub.2，并且是单键或双键。
• Clavulanic acid derivatives their preparation and use
  申请人：Beecham Group Limited

  公开号：US04372962A1

  公开（公告）日：1983-02-08

  The compounds of the formula (I): ##STR1## and pharmaceutically acceptable salts and in-vivo hydrolysable esters thereof wherein X is a sulphur atom or SO or SO.sub.2 group and R is a hydrogen atom or an alkyl group of 1 to 6 carbon atoms have been found to be .beta.-lactamase inhibitors and antibacterial agents. Their preparation and use is described.

  化合物的化学式（I）：##STR1##及其药用盐和体内可水解酯，其中X是硫原子或SO或SO.sub.2基团，R是氢原子或1至6个碳原子的烷基基团，已被发现是β-内酰胺酶抑制剂和抗菌剂。它们的制备和用途已经描述。
• Thiazine derivatives
  申请人：Nishimura Kazuo

  公开号：US06960575B2

  公开（公告）日：2005-11-01

  A compound having 3-oxo-3, 4-dihydro-2H-1, 4-thiazine 4-tetrahydropyrazine as a main skeleton. The compound is a chymase inhibitor and is represented by the following formula [I] and salts thereof: In the formula [I], X is S; R 1 and R 2 are H, alkyl, cycloalkyl or aryl; R 3 and R 4 are H, alkyl, cycloalkyl, aryl or an aromatic heterocycle; R 5 is H, alkyl, cycloalkyl, aryl or -A 3 -A 4 -R 7 ; R 6 is H, alkyl, cycloalkyl, hydroxy, alkoxy, aryl, aryloxy or an aromatic heterocycle; R 7 is H, alkyl, hydroxy, alkoxy, aryl, aryloxy, amino, alkylamino, arylamino, an aromatic heterocycle or a nonaromatic heterocycle; A 1 is alkylene; A 2 is carbonyl or sulfonyl; A 3 is alkylene; A 4 is carbonyl or oxalyl; and n is 0 or 1.

  一种具有3-氧代-3，4-二氢-2H-1，4-噻嗪-4-四氢吡嗪为主要骨架的化合物。该化合物是一种胰蛋白酶酶抑制剂，其化学式[I]及其盐如下所示：在公式[I]中，X为S；R1和R2为H，烷基，环烷基或芳基；R3和R4为H，烷基，环烷基，芳基或芳香族杂环；R5为H，烷基，环烷基，芳基或-A3-A4-R7；R6为H，烷基，环烷基，羟基，烷氧基，芳基，芳氧基或芳香族杂环；R7为H，烷基，羟基，烷氧基，芳基，芳氧基，氨基，烷基氨基，芳基氨基，芳香族杂环或非芳香族杂环；A1为烷基；A2为羰基或磺酰基；A3为烷基；A4为羰基或草酰基；n为0或1。
• 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.
• Nucleosides of 1,4-thiazin-3-one and derivatives as tetrahedral intermediate analogs of enzymes in pyrimidine nucleoside metabolism
  作者：E. Ted Marcus、Afaf Gundy、Corey H. Levenson、Rich B. Meyer

  DOI：10.1021/jm00403a015

  日期：1988.8

  Reaction of the trimethylsilylated derivative of 1,4-thiazin-3-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose in the presence of SnCl4 gave, after deblocking, 4-beta-ribofuranosyl-1,4-thiazin-3-one (8). Treatment of 1,4-thiazin-3-one with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-alpha-D-erythro-pentofuranose in the presence of sodium hydride provided, after deblocking, the corresponding 2-deoxy-beta-D-ribofuranosyl derivatives (19). Oxidation of 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one (7) with 1 equiv of m-chloroperbenzoic acid resulted in 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazine-2,3-dione (9) and 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one 1-oxide (10). Evidence is presented that indicates that the oxidation of the thiazine at the 2-position is due to a Pummerere rearrangement. The new compounds failed to show significant activity against tumor cell lines in culture, L1210 cells in vivo, virus cytotoxicity in cell culture, or cytidine deaminase.