4-(2-methyl-1H-pyrrol-4-yl)-2-(2-guanidino)thiazole | 115027-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2-methyl-1H-pyrrol-4-yl)-2-(2-guanidino)thiazole
• 英文别名: N-[4-(5-Methyl-1H-pyrrol-3-yl)-thiazol-2-yl]-guanidine；2-[4-(5-methyl-1H-pyrrol-3-yl)-1,3-thiazol-2-yl]guanidine
• CAS: 115027-84-4
• 化学式: C₉H₁₁N₅S
• 分子量: 221.286
• InChiKey: ZQDQRJJOHRLAJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(2-氯乙酰基)-1H-吡咯-2-甲醛 在 盐酸 、 diborane(6) 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-(2-methyl-1H-pyrrol-4-yl)-2-(2-guanidino)thiazole
  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

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.

  公式为 ##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盐；其中R.sup.1是氢，(C.sub.1 -C.sub.10)烷基，可选取取代的苯基或某些可选取取代的芳基烷基基团；R.sup.2是氢或(C.sub.1 -C.sub.4)烷基，Ar是某些可选取取代的吡咯基或吲哚基团；用于治疗胃溃疡的方法，通过抑制壁细胞H.sup.+ /K.sup.+ ATP酶，以及与吡罗昔康联合用于治疗哮喘等炎症病症，适用于哺乳动物，并含有该化合物的制药组合物。
• 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
• US5026715A
  申请人：——

  公开号：US5026715A

  公开（公告）日：1991-06-25