1-(N-benzylguanyl)thiourea | 101190-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(N-benzylguanyl)thiourea
• 英文别名: (N-Benzylguanyl)thiourea；benzylguanylthiourea；(N'-benzylcarbamimidoyl)thiourea
• CAS: 101190-77-6
• 化学式: C₉H₁₂N₄S
• 分子量: 208.287
• InChiKey: KGZHTIHJUAVJOC-UHFFFAOYSA-N

物化性质

• 沸点：
  344.7±35.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-氯-1-(2-甲基-1H-吲哚-3-基)-乙酮 、 1-(N-benzylguanyl)thiourea 以 乙醇 为溶剂， 生成 2-benzyl-1-[4-(2-methyl-1H-indol-3-yl)-1,3-thiazol-2-yl]guanidine
  参考文献：
  名称：

  Antiulcer agents. 4-Substituted 2-guanidinothiazoles: reversible, competitive, and selective inhibitors of gastric H+,K+-ATPase

  摘要：

  A series of 4-substituted 2-guanidinothiazoles has been found to inhibit the gastric proton-pump enzyme H+,K(+)-ATPase. In general, these compounds were reversible inhibitors of canine gastric H+,K(+)-ATPase, competitive at the K+ site, and selective relative to canine renal Na+,K(+)-ATPase. Structure-activity relationship (SAR) studies on this series revealed no general replacement for the guanidinothiazole. On the other hand, use of pyrrolyl, phenyl, and indolyl groups as the C-4 substituent yielded active compounds. Extensive studies of substitution patterns on these 4-aryl groups led to more active compounds, but no consistent SAR became apparent. Monosubstitution of the guanidine and substitution of the thiazole at C-5 both often led to increased activity, but combining these changes generated compounds less active than the parents. Despite 100-fold improvement in in vitro inhibitory potency, only a 3-fold increase in gastric antisecretory activity in rats was observed for these agents.

  DOI：

  10.1021/jm00164a012
• 作为产物：
  描述：

  S-Methyldithiobiuretium iodide 、 苄胺 在 sodium acetate 作用下， 以 异丙醇 为溶剂， 生成 1-(N-benzylguanyl)thiourea
  参考文献：
  名称：

  Process for preparing substituted guanylthioureas

  摘要：

  公开号：

  EP0357192B1

文献信息

• 2-guanidino-4-arylthiazoles for treatment of peptic ulcers
  申请人：Pfizer Inc.

  公开号：US05026715A1

  公开（公告）日：1991-06-25

  2-Guanidino-4-arylthiazole compounds of the formula ##STR1## a pharmaceutically acceptable cationic or acid addition salt thereof wherein R.sup.1 is hydrogen, (C.sub.1 -C.sub.10)alkyl, optionally substituted phenyl or certain optionally substituted aralkyl groups; R.sup.2 is hydrogen or (C.sub.1 -C.sub.4)alkyl, and Ar is certain optionally substituted pyrrolyl or indolyl groups; method for their use in treatment of gastric ulcers, by inhibition of parietal cell H.sup.+ /K.sup.+ ATPase, and antiinflammatory conditions in combination with piroxicam, for use in mammals, and pharmaceutical compositions containing said compounds.

  式为##STR1##的2-鸟氨酸基-4-芳基噻唑化合物及其药学上可接受的阳离子或酸加合物盐，其中R.sup.1为氢、(C.sub.1 -C.sub.10)烷基、可选择取代苯基或某些可选择取代的芳基烷基基团；R.sup.2为氢或(C.sub.1 -C.sub.4)烷基，Ar为某些可选择取代的吡咯基或吲哚基团；其在治疗胃溃疡中的应用方法，通过抑制壁细胞H.sup.+ /K.sup.+ ATP酶，以及与哌替考结合用于治疗哮喘炎症状的条件，用于哺乳动物，并含有上述化合物的药物组合物。
• Improved formulation of antiinflammatory drugs
  申请人：PFIZER INC.

  公开号：EP0178121A2

  公开（公告）日：1986-04-16

  An improved antiinflammatory composition and method of treating inflammation which employs a combination of an antiinflammatory agent (e.g. indomethacin or an oxicam) with a histamine-H2 antagonist selected from the group consisting of 2-guanidino-4-(4-imidazolyl)thiazole, 2-guanidino-4-(2-methyl-4-imidazolyl)thiazofe, 2-(N-benzyl-N'-guanidino)-4-(2--methyl-4-imidazolyl)thiazole, 2-(N-pentyl-N'-guanidino)-4-(2--methyl-4-imidazolyl)thiazole and 2-guanidino-4-[2-hexyt- aminol-4-imidazolyl]thiazole.

  一种改进的抗炎组合物和治疗炎症的方法，它采用了一种抗炎剂（如吲哚美辛或奥昔康）与组胺-H2 拮抗剂的组合。2-胍基-4-(4-咪唑基)噻唑、2-胍基-4-(2-甲基-4-咪唑基)噻唑2-(N-苄基-N'-胍基)-4-(2-甲基-4-咪唑基)噻唑、2-(N-戊基-N'-胍基)-4-(2-甲基-4-咪唑基)噻唑和 2-胍基-4-[2-己基氨基-4-咪唑基]噻唑。
• Synthesis of Mono N-Substituted Guanylthioureas
  作者：Lawrence A. Reiter、Katherine E. Brighty、Rhonda A. Bryant、Miriam E. Goldsmith

  DOI：10.1080/00397919608003504

  日期：1996.4

  A convenient method for the synthesis of mono N-substituted guanylthioureas in reasonable yields from readily available starting materials has been developed. In contrast to the previously published method, the use of highly noxious hydrogen sulfide is avoided. The method allows the rapid preparation of guanylthioureas since the synthesis of each requires only a single step from a common intermediate, the S-methylated derivative of dithiobiuret.
• 2-Guanidino-4-arylthiazoles for treatment of peptic ulcers
  申请人：PFIZER INC.

  公开号：EP0259085B1

  公开（公告）日：1991-08-21
• US4636498A
  申请人：——

  公开号：US4636498A

  公开（公告）日：1987-01-13