5-propyl>>amino-1-methyl-1H-tetrazole | 82436-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-propyl>>amino-1-methyl-1H-tetrazole
• 英文别名: 1-methyl-N-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]tetrazol-5-amine
• CAS: 82436-33-7
• 化学式: C₁₇H₂₆N₆O
• 分子量: 330.433
• InChiKey: CPSWKXUMDDURJT-UHFFFAOYSA-N

物化性质

• 沸点：
  506.6±60.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰胺,2-氯-N-[3-[3-(1-哌啶基甲基)苯氧基]丙基]- 在 盐酸 、 氢氧化钾 、 甲烷磺酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 34.5h， 生成 5-propyl>>amino-1-methyl-1H-tetrazole
  参考文献：
  名称：

  Antiulcer Agents. II. Synthesis and Gastric Acid Antisecretory Activity of N-(3-{3-(Piperidinomethyl)phenoxy}propyl)-4-(1-methyl-1H-tetrazol-5-ylthio)butanamide and Related Compounds.

  摘要：

  本研究制备了以 1-甲基-1H-四唑-5-硫基为药理基础的 N-[3-{3-(哌啶甲基)苯氧基}丙基]丁酰胺类化合物及相关化合物，并测试了它们对患有胃瘘的清醒大鼠组胺诱导的胃酸分泌的抗分泌活性。大多数化合物都显示出了抗分泌活性。其中，N-[3-{3-(哌啶甲基)苯氧基}丙基]-4-(1-甲基-1H-四唑-5-硫基)丁酰胺（5f）具有最强的活性，并表明了甲氧基羰基被 1-甲基-1H-四唑-5-基团等位取代的可能性。此外，还讨论了结构-活性关系。

  DOI：

  10.1248/cpb.39.1430

文献信息

• Smiles Rearrangement of 2-(1-Methyl-1H-tetrazol-5-ylthio)acetamides and Their Sulfonyl Derivatives.
  作者：Katsuyuki ISHII、Minoru HATANAKA、Ikuo UEDA

  DOI：10.1248/cpb.39.3331

  日期：——

  The Smiles rearrangement of 2-(1-methyl-1H-tetrazol-5-ylthio)acetamides and their sulfonyl derivatives occurred under basic conditions to yield 5-amino-1-methyl-1H-tetrazole derivatives in excellent yields.

  在碱性条件下，2-(1-甲基-1H-四唑-5-基硫基)乙酰胺及其磺酰衍生物的斯迈尔斯重排反应产生了5-氨基-1-甲基-1H-四唑衍生物，得率极高。
• 5-Amino-tetrazole derivatives, processes for their preparation and pharmaceutical compositions containing them
  申请人：GLAXO GROUP LIMITED

  公开号：EP0049049A1

  公开（公告）日：1982-04-07

  The invention relates to compounds of the general formula (I) and physiologically acceptable salts, hydrates and bioprecursors thereof in which R, represents C1-14 alkyl, cycloalkyl, aralkyl, trifluoroalkyl, heteroaralkyl, alkenyl, alkynyl, or alkyl substituted by hydroxy, alkoxy, amino, alkylamino, dialkylamino or cycloalkyl; and R2 represents hydrogen or a C1-4 alkyl group; or R1 and R2 together with the nitrogen atom to which they are attached form a 5-10 membered ring which may be saturated or may contain at least one double bond, may be unsubstituted or may be substituted by one or more C1-3 alkyl groups or a hydroxy group and/or may contain another heteroatom selected from oxygen and sulphur; Alk represents a straight or branched C1-6 alkylene chain. Q represents a furan or thiophen ring in which incorporation into the rest of the molecule is through bonds at the 2- and 5-positions the furan or thiophen ring optionally bearing a further substituent R4 adjacent to the group R1R2N-Alkyl-; or 0 represents a thiophen ring in which incorporation into the rest of the molecule is through bonds at the 2- and 4-positions, the thiophen ring optionally bearing a further substituent R4 adjacent to the group R1R2NAlk with the proviso that when the group R1R2NAIlk is in the 4-position then the group R4 is in the 5-position; or Q represents a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3- or 1- and 4-positions; R4 represents halogen or C,., alkyl which may be substituted by hydroxy or C1-4 alkoxy; R3 represents hydrogen, alkyl, alkenyl, aralkyl, C2-6 alkyl substituted by hydroxy, alkoxy or C,., alkanoyloxy; X and Y, which may be the same or different, each represent oxygen, sulphur, methylene or a bond; n represents zero, 1, 2 or 3 and m represents an interger from 2 to 5 with the provisos that (a) the total number of atoms in the chain X(CH2)nY(CH2)m is an integer from 3 to 8 and (b) when X and Y represent oxygen or sulphur then n is 2 or 3. The compounds show pharmacological activity as selective histamine H2-antagonists.

  本发明涉及通式 (I) 的化合物 及其生理上可接受的盐、水合物和生物前体，其中 R，代表 C1-14 烷基、环烷基、芳基、三氟烷基、杂烷基、烯基、炔基或被羟基、烷氧基、氨基、烷基氨基、二烷基氨基或环烷基取代的烷基；R2 代表氢或 C1-4 烷基；或 R1 和 R2 与它们所连接的氮原子一起形成一个 5-10 个成员的环，该环可以是饱和的，也可以含有至少一个双键，可以是未取代的，也可以被一个或多个 C1-3 烷基或羟基取代，和/或可以含有另一个选自氧和硫的杂原子； 烷基代表直链或支链 C1-6 亚烷基链。 Q 代表呋喃环或噻吩环，通过 2-位和 5-位的键与分子的其余部分结合，呋喃环或噻吩环可选择带有与基团 R1R2N-Alkyl- 相邻的另一个取代基 R4；或 0 代表噻吩环，通过 2 位和 4 位的键与分子的其余部分结合，该噻吩环可选择带有与基团 R1R2NAlk 相邻的另一个取代基 R4，但当基团 R1R2NAIlk 位于 4 位时，基团 R4 位于 5 位；或 Q 代表苯环，通过 1 位和 3 位或 1 位和 4 位的键与分子的其余部分结合； R4 代表卤素或可被羟基或 C1-4 烷氧基取代的 C,...烷基； R3 代表氢、烷基、烯基、芳烷基、被羟基、烷氧基或 C...烷酰氧基取代的 C2-6 烷基； X 和 Y 可以相同或不同，各自代表氧、硫、亚甲基或键； n 代表零、1、2 或 3，m 代表 2 至 5 之间的整数，但前提是：(a) 链中 X(CH2)nY(CH2)m 的原子总数为 3 至 8 之间的整数；(b) 当 X 和 Y 代表氧或硫时，n 为 2 或 3。 这些化合物具有选择性组胺 H2-拮抗剂的药理活性。
• CAREY, L.;PRICE, B. J.;CLITHAROW, J. W.;BRADSHAW, J.;MARTIN-SMITH, M.
  作者：CAREY, L.、PRICE, B. J.、CLITHAROW, J. W.、BRADSHAW, J.、MARTIN-SMITH, M.

  DOI：——

  日期：——
• Antiulcer Agents. II. Synthesis and Gastric Acid Antisecretory Activity of N-(3-{3-(Piperidinomethyl)phenoxy}propyl)-4-(1-methyl-1H-tetrazol-5-ylthio)butanamide and Related Compounds.
  作者：Ikuo UEDA、Katsuyuki ISHII、Katsuo SINOZAKI、Masao SEIKI、Minoru HATANAKA

  DOI：10.1248/cpb.39.1430

  日期：——

  N-[3-3-(Piperidinomethyl)phenoxy}propyl]butanamides having a 1-methyl-1H-tetrazol-5-ylthio moiety as a pharmacophore and related compounds were prepared and tested for their antisecretory activity against histamine-induced gastric acid secretion in conscious rats with gastric fistulas. Most of the compounds showed antisecretory activity. Among them, N-[3-3-(piperidinomethyl)phenoxy}propyl]-4-(1-methyl-1H-tetrazol-5-ylthio)butanamide (5f) was found to possess the most potent activity, and a possibility of isosteric replacement of the methoxycarbonyl group with 1-methyl-1H-tetrazol-5-yl group was indicated. The structure-activity relationships are also discussed.

  本研究制备了以 1-甲基-1H-四唑-5-硫基为药理基础的 N-[3-3-(哌啶甲基)苯氧基}丙基]丁酰胺类化合物及相关化合物，并测试了它们对患有胃瘘的清醒大鼠组胺诱导的胃酸分泌的抗分泌活性。大多数化合物都显示出了抗分泌活性。其中，N-[3-3-(哌啶甲基)苯氧基}丙基]-4-(1-甲基-1H-四唑-5-硫基)丁酰胺（5f）具有最强的活性，并表明了甲氧基羰基被 1-甲基-1H-四唑-5-基团等位取代的可能性。此外，还讨论了结构-活性关系。