[2-(2-methoxyphenyl)ethylamidino]thiourea

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [2-(2-methoxyphenyl)ethylamidino]thiourea
• 英文别名: [N'-[2-(2-methoxyphenyl)ethyl]carbamimidoyl]thiourea
• 化学式: C₁₁H₁₆N₄OS
• 分子量: 252.34
• InChiKey: VYDYLRJJWPBNIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酰胺,N-[[6-(溴乙酰基)-2-吡啶基]甲基]- 、 [2-(2-methoxyphenyl)ethylamidino]thiourea 以 乙腈 为溶剂， 反应 1.0h， 以48%的产率得到N-[[6-[2-[[N'-[2-(2-methoxyphenyl)ethyl]carbamimidoyl]amino]-1,3-thiazol-4-yl]pyridin-2-yl]methyl]acetamide
  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：

  脒基硫脲 、 2-甲氧基苯乙胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 22.0h， 以30%的产率得到[2-(2-methoxyphenyl)ethylamidino]thiourea
  参考文献：
  名称：

  Anti-Helicobacter pylori Agents. 3. 2-[(Arylalkyl)guanidino]-4-furylthiazoles

  摘要：

  A series of 2-[(arylalkyl)guanidinol-4-[(5-acetamidomethyl)furan-2-yl]thiazoles and some 4-acetamidomethyl positional isomers were synthesized and evaluated for antimicrobial activity against Helicobacter pylori. Among the compounds that had potent antimicrobial activity (MIC < 0.1 mu g/mL), compounds 31 and 36 additionally possessed H2 antagonist and gastric antisecretory activities. Though compound 51, an analogue incorporating a methyl group onto the furan nucleus of 36, and compound 54, a positional isomer of 51, also showed potent anti-H. pylori activity, the H2 antagonism profile was eliminated from these compounds. Thus, two types of potent anti-H. pylori agents could be derived from the same scaffold.

  DOI：

  10.1021/jm9900671

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。
• [EN] FURYLTHIAZOLE AND THEIR USE AS H2-RECEPTOR ANTAGONISM AND ANTIMICROBIAL<br/>[FR] FURYLTHIAZOLES ET LEUR UTILISATION EN TANT QU'ANTAGONISTES DES RECEPTEURS H2 ET ANTIMICROBIENS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1995018126A1

  公开（公告）日：1995-07-06

  (EN) This invention relates to furylthiazole derivatives represented by formula (I), wherein each symbol is as defined in the specification and pharmaceutically acceptable salts thereof which have antiulcer activity, H2-receptor antagonism and antimicrobial activity, to processes for the preparation thereof, to a pharmaceutical composition comprising the same and to a method for the treatment of ulcer and infectious diseases in human being or animals.(FR) L'invention concerne des dérivés furylthiazoles représentés par la formule (I), dans laquelle chaque symbole correspond à la définition donnée dans la description, ainsi que des sels pharmaceutiquement acceptables desdits dérivés, qui présentent une activité antiulcéreuse et constituent des antagonistes des récepteurs H2 et des antimicrobiens. L'invention concerne également des procédés de préparation de tels dérivés, une composition pharmaceutique les contenant, et un procédé de traitement des ulcères et des maladies infectieuses chez l'homme et les animaux.

  该发明涉及由公式（I）表示的呋喃噻唑衍生物，其中每个符号如规范中定义的那样，以及其药学上可接受的盐，具有抗溃疡活性、H2受体拮抗和抗微生物活性，以及制备这些衍生物的方法，包括含有这些衍生物的制药组合物，以及用于治疗人类或动物的溃疡和传染性疾病的方法。
• Anti-<i>Helicobacter </i><i>p</i><i>ylori</i> Agents. 5. 2-(Substituted guanidino)-4-arylthiazoles and Aryloxazole Analogues
  作者：Yousuke Katsura、Shigetaka Nishino、Yoshikazu Inoue、Kazuo Sakane、Yoshimi Matsumoto、Chizu Morinaga、Hirohumi Ishikawa、Hisashi Takasugi

  DOI：10.1021/jm010217j

  日期：2002.1.1

  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.
• Anti-<i>Helicobacter pylori</i> Agents. 3. 2-[(Arylalkyl)guanidino]-4-furylthiazoles
  作者：Yousuke Katsura、Shigetaka Nishino、Mitsuko Ohno、Kazuo Sakane、Yoshimi Matsumoto、Chizu Morinaga、Hirohumi Ishikawa、Hisashi Takasugi

  DOI：10.1021/jm9900671

  日期：1999.7.1

  A series of 2-[(arylalkyl)guanidinol-4-[(5-acetamidomethyl)furan-2-yl]thiazoles and some 4-acetamidomethyl positional isomers were synthesized and evaluated for antimicrobial activity against Helicobacter pylori. Among the compounds that had potent antimicrobial activity (MIC < 0.1 mu g/mL), compounds 31 and 36 additionally possessed H2 antagonist and gastric antisecretory activities. Though compound 51, an analogue incorporating a methyl group onto the furan nucleus of 36, and compound 54, a positional isomer of 51, also showed potent anti-H. pylori activity, the H2 antagonism profile was eliminated from these compounds. Thus, two types of potent anti-H. pylori agents could be derived from the same scaffold.