5,6-dihydro-4H-[1,3]thiazin-2-ylamine; hydrochloride | 2799-74-8

• 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: 5,6-dihydro-4H-[1,3]thiazin-2-ylamine; hydrochloride
• 英文别名: 5,6-Dihydro-4H-[1,3]thiazin-2-ylamin; Hydrochlorid；2-Amino-5,6-dihydro-4H-1,3-thiazin-hydrochlorid；1,3-Thiazinan-2-imine hydrochloride；5,6-dihydro-4H-1,3-thiazin-2-amine;hydrochloride
• CAS: 2799-74-8
• 化学式: C₄H₈N₂S*ClH
• 分子量: 152.648
• InChiKey: XSVRZUUQQSNMCN-UHFFFAOYSA-N

物化性质

• 熔点：
  153-154 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-4H-[1,3]thiazin-2-ylamine; hydrochloride 生成 1.1'--3,3'-bis(thioharnstoff)
  参考文献：
  名称：

  2-Amino-2-thiazoline. IV. Ring-opening of 2-amino-2-thiazolines and 2-amino-2-selenazoline with hydrogen sulfide to form thiourea derivatives

  摘要：

  DOI：

  10.1021/jo01266a102
• 作为产物：
  描述：

  potassium thioacyanate 、 3-氯丙胺盐酸盐 以 水 为溶剂， 反应 2.0h， 以55%的产率得到5,6-dihydro-4H-[1,3]thiazin-2-ylamine; hydrochloride
  参考文献：
  名称：

  2-Iminopiperidine and Other 2-Iminoazaheterocycles as Potent Inhibitors of Human Nitric Oxide Synthase Isoforms

  摘要：

  A series of 2-iminoazaheterocycles. have been prepared and shown to be patent inhibitors of human nitric oxide synthase (NOS) isoforms. This series includes cyclic amidines ranging from five- to nine-membered rings, of which 2-iminopiperidine and 2-iminohomopiperidine were the most potent inhibitors, with IC50 values of 1.0 and 2.0 mu M, respectively, for human inducible nitric oxide synthase. This series of cyclic inhibitors was further expanded to include analogs with heteroatoms in the S-position of the six-membered ring. This modification was tolerated for sulfur and oxygen, but nitrogen reduced the inhibitory potency. The oral administration of 2-iminopiperidine in lipopolysaccharide (LPS)-treated rats inhibited the LPS-induced increase in plasma nitrite/nitrate levels in a dose-dependent manner, demonstrating its ability to inhibit inducible NOS activity in vivo. These cyclic amidines represent a new class of potent NOS inhibitors and the foundation for potential therapeutic agents.

  DOI：

  10.1021/jm950766n

文献信息

• Schoeberl,A.; Magosch,K.-H., Justus Liebigs Annalen der Chemie, 1970, vol. 742, p. 74 - 84
  作者：Schoeberl,A.、Magosch,K.-H.

  DOI：——

  日期：——
• 2-Amino-2-thiazoline. VII. Unequivocal structure assignment of the products of the reaction of 2-amino-2-thiazoline and its analogs with carbethoxy isothiocyanate
  作者：Daniel L. Klayman、Thomas S. Woods

  DOI：10.1021/jo00927a007

  日期：1974.6
• 2-Iminopiperidine and Other 2-Iminoazaheterocycles as Potent Inhibitors of Human Nitric Oxide Synthase Isoforms
  作者：William M. Moore、R. Keith Webber、Kam F. Fok、Gina M. Jerome、Jane R. Connor、Pamela T. Manning、Pamela S. Wyatt、Thomas P. Misko、Foe S. Tjoeng、Mark G. Currie

  DOI：10.1021/jm950766n

  日期：1996.1.1

  A series of 2-iminoazaheterocycles. have been prepared and shown to be patent inhibitors of human nitric oxide synthase (NOS) isoforms. This series includes cyclic amidines ranging from five- to nine-membered rings, of which 2-iminopiperidine and 2-iminohomopiperidine were the most potent inhibitors, with IC50 values of 1.0 and 2.0 mu M, respectively, for human inducible nitric oxide synthase. This series of cyclic inhibitors was further expanded to include analogs with heteroatoms in the S-position of the six-membered ring. This modification was tolerated for sulfur and oxygen, but nitrogen reduced the inhibitory potency. The oral administration of 2-iminopiperidine in lipopolysaccharide (LPS)-treated rats inhibited the LPS-induced increase in plasma nitrite/nitrate levels in a dose-dependent manner, demonstrating its ability to inhibit inducible NOS activity in vivo. These cyclic amidines represent a new class of potent NOS inhibitors and the foundation for potential therapeutic agents.
• 2-Amino-2-thiazoline. IV. Ring-opening of 2-amino-2-thiazolines and 2-amino-2-selenazoline with hydrogen sulfide to form thiourea derivatives
  作者：Daniel L. Klayman、Peter T. McIntyre

  DOI：10.1021/jo01266a102

  日期：1968.2