2-(2-pyridylmethyl)isothiourea dihydrochloride | 1822-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(2-pyridylmethyl)isothiourea dihydrochloride
• 英文别名: pyridin-2-ylmethyl carbamimidothioate;hydrochloride
• CAS: 1822-49-7
• 化学式: C₇H₉N₃S*2ClH
• 分子量: 240.156
• InChiKey: MHUXBEIHGVVZGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-pyridylmethyl)isothiourea dihydrochloride 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 1.33h， 生成 2-(2-pyridyl)tetrahydrothiopyran
  参考文献：
  名称：

  Synthesis and antisecretory and antiulcer activities of derivatives and analogs of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide

  摘要：

  New thioamide derivatives of 2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (29) and related compounds (in which the tetrahydrothiophene ring was replaced by tetrahydrothiopyran, tetrahydrofuran, 1,3-dithiane, or 1,3-oxathiane and where the pyridine ring was replaced by other nitrogen heterocycles) were synthesized and tested for their antisecretory and antiulcer activities. These thioamides were prepared according to one of the following methods: reaction of an isothiocyanate with the carbanion of the corresponding cyclic precursor (for secondary thioamides); reaction of ammonia or an amine with the dithio ester prepared from the same precursor (for primary, secondary, and tertiary thioamides). These thioamides were evaluated by the Shay method to measure their antisecretory activity and by the stress-induced-ulcer method to test their antiulcer activity. Structure-activity relationships are discussed. N-Methyl-2-(2-pyridyl)tetrahydrothiophene-2-carbothioamide (R.P. 40749, 30) exhibited activities that were at least 10 times higher than those reported for cimetidine.

  DOI：

  10.1021/jm00384a004
• 作为产物：
  描述：

  2-氯甲基吡啶盐酸盐 、 硫脲 以 乙醇 为溶剂， 以71%的产率得到2-(2-pyridylmethyl)isothiourea dihydrochloride
  参考文献：
  名称：

  3-硫代取代基对亚苄基定向甘露糖基化的影响。桥联吡啶离子的分离和 3-O-Picolyl 和 3-S-Picolyl 酯的影响

  摘要：

  氧取代 4,6- O-亚苄基保护的吡喃甘露糖基硫代糖苷 3 位硫的影响显示出相当大的保护基依赖性变化。值得注意的是，3- S-甲基吡啶酯是 α-导向的，这与相应的 3- O-甲基吡啶基系统的 β-导向作用形成对比。3- S-甲基吡啶基取代系统的活化导致稳定的七元桥联双环吡啶鎓离子的分离。

  DOI：

  10.1002/ejoc.202200320

文献信息

• Pyrimidin-aminomethyl-pyridine derivatives, their preparation and their use in the control of helicobacter bacteria
  申请人：BYK Gulden Lomberg Chemische Fabrik GmbH

  公开号：US06395732B1

  公开（公告）日：2002-05-28

  The present invention relates to compounds of formula (I) wherein R1, R2, and R3 are hydrogen, 1-4C-alkyl, or halogen; R4, R5, R6, and R9 are hydrogen or 1-4C-alkyl; R7 and R8 are hydrogen, 1-4C-alkyl, 1-4C-alkoxy, or halogen; A is 1-7C-alkylene, 2-7C-alkenylene, 3-7C-cycloalkylene, or phenylene; G is hydrogen, hydroxyl, 1-7C-alkyl, 1-4C-alkyl substituted by fluorine, 2-7C-alkenyl, 3-7C-cycloalkyl, a mono- or di-1-4C-alkylcarbamoyl or -thiocarbamoyl, N-1-4C-alkyl-N′-cyanoamidino, 1-N-1-4C-alkylamino-2-nitroethylene, N-2-propynyl-N′-cyanoamidino, aminosulfonylamidino, —N(R10)R11, the part of the compound of formula (I) bonded to A, glucopyranoside, or a cyclic system or bicyclic system which is optionally substituted by R12 and R13; X is oxygen, N-1-4C-alkyl, NH, or S; Y is oxygen, N-1-4C-alkyl, NH, S, 1,4-piperazinylene, or 1,4-piperidinylene; Z is oxygen, N-1-4C-alkyl, NH, S, or CO; m is from 1 to 7; n is from 0 to 4; t is 0, 1, or 2; and u is 0 or 1, and their salts suitable for controlling Helicobacter bacteria.

  本发明涉及式(I)的化合物，其中R1、R2和R3为氢、1-4C-烷基或卤素；R4、R5、R6和R9为氢或1-4C-烷基；R7和R8为氢、1-4C-烷基、1-4C-烷氧基或卤素；A为1-7C-烷基、2-7C-烯基、3-7C-环烷基或苯基；G为氢、羟基、1-7C-烷基、受氟取代的1-4C-烷基、2-7C-烯基、3-7C-环烷基、一或二个1-4C-烷基氨基甲酰基或硫代氨基甲酰基、N-1-4C-烷基-N′-氰基氨基甲酰基、1-N-1-4C-烷基氨基-2-硝基乙烯、N-2-丙炔基-N′-氰基氨基甲酰基、氨基磺酰氨基甲酰基、—N(R10)R11，与A结合的式(I)化合物的部分、葡萄糖吡喃苷或可选择由R12和R13取代的环状系统或双环系统；X为氧、N-1-4C-烷基、NH或S；Y为氧、N-1-4C-烷基、NH、S、1,4-哌嗪亚烷基或1,4-哌啶亚烷基；Z为氧、N-1-4C-烷基、NH、S或CO；m为1至7；n为0至4；t为0、1或2；u为0或1，及其适用于控制幽门螺杆菌的盐。
• Quinoline-aminomethyl-pyridyl derivatives with anti-helicobacter activity
  申请人：Altana Pharma AG

  公开号：US06479514B1

  公开（公告）日：2002-11-12

  Compounds of formula (I) in which the substituents and symbols have the meanings indicated in the description, are suitable for the control of Helicobacter bacteria.

  式（I）中的化合物，其中取代基和符号具有描述中指示的含义，适用于控制幽门螺杆菌。
• Adamantyl Ethanone Pyridyl Derivatives: Potent and Selective Inhibitors of Human 11β-Hydroxysteroid Dehydrogenase Type 1
  作者：Xiangdong Su、Fabienne Pradaux-Caggiano、Nigel Vicker、Mark P. Thomas、Heather Halem、Michael D. Culler、Barry V. L. Potter

  DOI：10.1002/cmdc.201100182

  日期：2011.9.5

  such as type 2 diabetes and obesity. 11β‐Hydroxysteroid dehydrogenase type 1 (11β‐HSD1) catalyses the intracellular conversion of inactive cortisone to cortisol. Selective 11β‐HSD1 inhibitors have shown beneficial effects in various conditions, including diabetes, dyslipidemia and obesity. A series of adamantyl ethanone pyridyl derivatives has been identified, providing potent and selective inhibitors

  活性糖皮质激素水平升高与代谢综合征的几种表型的发展有关，例如 2 型糖尿病和肥胖症。11β-羟基类固醇脱氢酶 1 (11β-HSD1) 催化细胞内无活性的可的松转化为皮质醇。选择性 11β-HSD1 抑制剂已在多种疾病中显示出有益效果，包括糖尿病、血脂异常和肥胖症。已经鉴定了一系列金刚乙酮吡啶基衍生物，提供了有效和选择性的人 11β-HSD1 抑制剂。先导化合物对人和小鼠 11β-HSD1 显示出低纳摩尔抑制，并且对该亚型具有选择性，对 11β-HSD2 和 17β-HSD1 没有活性。构效关系研究表明，未取代的吡啶通过醚或亚砜接头连接到金刚乙酮基序上，为活性提供了合适的药效团。最有效的抑制剂具有 IC50值在 34–48 n M左右对抗人类 11β-HSD1，在人类肝微粒体中表现出合理的代谢稳定性，以及对关键人类 CYP450 酶的弱抑制。
• 2-(Pyrid-2-yl)tetrahydrothiophene derivatives
  申请人：Rhone-Poulenc Industries

  公开号：US04272534A1

  公开（公告）日：1981-06-09

  Compounds of the formula: ##STR1## wherein R represents hydrogen or alkyl of 1 through 4 carbon atoms, and R.sub.1 and R.sub.2 represent hydrogen or alkyl of 1 through 15 carbon atoms, or alkyl of 1 through 15 carbon atoms substituted by one substituent selected from (i) hydroxy, (ii) alkylamino in which the alkyl radical is of 1 through 4 carbon atoms, (iii) dialkylamino in which the alkyl radicals are of 1 through 4 carbon atoms, (iv) phenyl, (v) carboxy, and (vi) alkoxycarbonyl in which the alkoxy radical is of 1 through 4 carbon atoms, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached represent a five- or six-membered heterocyclic radical, are new compounds. They possess pharmacological properties and are particularly useful in the treatment of gastro-intestinal ulcers.

  式子为：##STR1## 其中 R 代表氢或1至4个碳原子的烷基，R.sub.1 和 R.sub.2 代表氢或1至15个碳原子的烷基，或1至15个碳原子的烷基被选自以下一种取代基取代：(i) 羟基，(ii) 烷基胺，其中烷基基团为1至4个碳原子，(iii) 二烷基胺，其中烷基基团为1至4个碳原子，(iv) 苯基，(v) 羧基，以及 (vi) 烷氧羰基，其中烷氧基团为1至4个碳原子，或 R.sub.1 和 R.sub.2 与它们所连接的氮原子共同表示五元或六元杂环基团，这些化合物是新的。它们具有药理学特性，特别适用于治疗胃肠溃疡。
• Horiuchi, Jiro; Suzuki, Kazuo; Shitara, Eiki, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 4, p. 1080 - 1084
  作者：Horiuchi, Jiro、Suzuki, Kazuo、Shitara, Eiki、Niwa, Ryuji、Kato, Tetsuzo

  DOI：——

  日期：——