n-butylamidinothiourea | 71916-65-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫脲类
• 英文名称: n-butylamidinothiourea
• 英文别名: butylcarbamimidoyl-thiourea；N-Butyl-N'-thiocarbamoyl-guanidin；Butylcarbamimidoyl-thioharnstoff；(N-n-butylamidino)thiourea；(N'-butylcarbamimidoyl)thiourea
• CAS: 71916-65-9
• 化学式: C₆H₁₄N₄S
• 分子量: 174.27
• InChiKey: NWZYKHSNRMAZLI-UHFFFAOYSA-N

物化性质

• 熔点：
  144-145 °C
• 沸点：
  256.9±23.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  n-butylamidinothiourea 在 一水合肼 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.0h， 生成 N-[4-(2-Aminomethyl-pyrimidin-4-yl)-thiazol-2-yl]-N'-butyl-guanidine
  参考文献：
  名称：

  Anti-Helicobacter pylori Agents. 5. 2-(Substituted guanidino)-4-arylthiazoles and Aryloxazole Analogues

  摘要：

  To extend the SAR study of guanidinothiazoles as a structurally novel class of anti-H. pylori agents, a series of 2-(substituted guanidino)-4-arylthiazoles and some 4-aryloxazole analogues were synthesized and evaluated for antimicrobial activity against H. pylori, Some of them were also subjected to H2 antagonist and gastric antisecretory assays. Several arylthiazoles were identified as potent anti-H. pylori agents, and of these, thienylthiazole derivative 44 exhibited the strongest activity (MIC = 0.0065 mug/mL) among the compounds obtained in our guanidinothiazole studies. Although 44 was void of H2 antagonist activity, pyridylthiazole derivative 39 had both potent anti-H. pylori and H2 antagonist activities. Thiazolylthiazole derivative 46 also showed potent anti-H. pylori activity, but the H2 antagonist activity was weak. On the other hand, no attractive activities were found in pyrimidyl, oxazolyl, isoxazolyl, imidazolyl, and oxadiazolylthiazole derivatives. The anti-H. pylori activity of the aryloxazole analogues was weaker than those of the corresponding arylthiazole derivatives, though they had potent H2 antagonist activity.

  DOI：

  10.1021/jm010217j
• 作为产物：
  描述：

  N-cyano-N’-butylguanidine 在 甲醇 、 硫化氢 作用下， 生成 n-butylamidinothiourea
  参考文献：
  名称：

  Birtwell et al., Journal of the Chemical Society, 1948, p. 1650

  摘要：

  DOI：

文献信息

• Anti-<i>Helicobacter </i><i>p</i><i>ylori</i> Agents. 4. 2-(Substituted guanidino)-4-phenylthiazoles and Some Structurally Rigid Derivatives
  作者：Yousuke Katsura、Tetsuo Tomishi、Yoshikazu Inoue、Kazuo Sakane、Yoshimi Matsumoto、Chizu Morinaga、Hirohumi Ishikawa、Hisashi Takasugi

  DOI：10.1021/jm000169n

  日期：2000.8.1

  In order to find a new class of anti-Helicobacter pylori (H. pylori) agents, a series of 4-[(3-acetamido)phenyl]-2-(substituted guanidino)thiazoles and some structurally rigid analoges were synthesized and evaluated for antimicrobial activity against H. pylori. Among the compounds obtained, high anti-H. pyrori activities were observed in benzyl derivative 34 (MIC = 0.025 microg/mL) and phenethyl derivatives

  为了找到一类新型的幽门螺杆菌（H. pylori）药剂，合成了一系列4-[（3-乙酰氨基）苯基] -2-（取代的胍基）噻唑和一些结构刚性的类似物，并对其进行了评估。对幽门螺杆菌的抗菌活性。在获得的化合物中，高抗H值。在苄基衍生物34（MIC = 0.025微克/毫升）和苯乙基衍生物35和36（MIC = 0.037微克/毫升和0.017微克/毫升）中观察到吡咯活性。尽管烷基衍生物通常显示较低的活性，但是2-甲氧基乙基衍生物28保留了显着的活性（MIC = 0.32 microg / mL），并且还比雷尼替丁具有更强的胃分泌活性。通过在噻唑和具有烷基链的苯环之间桥连而进行的结构限制不能提高该系列的活性。
• Guanidine derivatives of imidazoles and thiazoles
  申请人：ICI Americas Inc.

  公开号：US04165378A1

  公开（公告）日：1979-08-21

  The invention relates to guanidine derivatives of imidazoles and thiazoles which are histamine H-2 antagonists and which inhibit the secretion of gastric acid, to methods for their manufacture, to pharmaceutical compositions containing them and to methods of using such guanidine derivatives and compositions. The guanidine derivatives are of the general formula I: ##STR1## in which X is S or NH, Y is O, S, or SO, m is 1 to 4 and n is suitably 1 to 4, R.sup.1 is hydrogen, halogen or alkyl, R.sup.2 is hydrogen, alkyl, alkanoyl or aroyl, A is a 3,4-dioxocyclobuten-1,2-diyl radical or C=Z in which Z is O, S, NCN, NNO.sub.2, CHNO.sub.2, NCONH.sub.2, C(CN).sub.2, NCOR.sup.3, NCO.sub.2 R.sup.3, NSO.sub.2 R.sup.3 or NR.sup.4 in which R.sup.3 is alkyl or aryl and R.sup.4 is hydrogen or alkyl, B is alkoxy or alkylthio or NR.sup.5 R.sup.6 in which R.sup.5 and R.sup.6 are independently hydrogen, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, alkoxyalkyl, alkylaminoalkyl or dialkylaminoalkyl; and the salts thereof.

  本发明涉及咪唑和噻唑的胍衍生物，它们是组胺H-2拮抗剂，可以抑制胃酸的分泌，涉及它们的制备方法，含有它们的制药组合物以及使用这些胍衍生物和组合物的方法。该胍衍生物的一般式为I：##STR1## 其中X为S或NH，Y为O，S或SO，m为1至4，n适宜为1至4，R.sup.1为氢，卤素或烷基，R.sup.2为氢，烷基，烷酰基或芳酰基，A为3,4-二氧代环丁烯-1,2-二基基团或C=Z，其中Z为O，S，NCN，NNO.sub.2，CHNO.sub.2，NCONH.sub.2，C(CN).sub.2，NCOR.sup.3，NCO.sub.2R.sup.3，NSO.sub.2R.sup.3或NR.sup.4，其中R.sup.3为烷基或芳基，R.sup.4为氢或烷基，B为烷氧基或烷硫基或NR.sup.5R.sup.6，其中R.sup.5和R.sup.6独立地为氢，烷基，烯基，环烷基，羟基烷基，烷氧基烷基，烷基氨基烷基或二烷基氨基烷基；以及它们的盐。
• Birtwell et al., Journal of the Chemical Society, 1948, p. 1650
  作者：Birtwell et al.

  DOI：——

  日期：——
• US4165378A
  申请人：——

  公开号：US4165378A

  公开（公告）日：1979-08-21
• US4262126A
  申请人：——

  公开号：US4262126A

  公开（公告）日：1981-04-14