2-cyano-1-methyl-3-[4-(2-methyl-1H-imidazol-4-yl)butyl]guanidine | 112357-45-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyano-1-methyl-3-[4-(2-methyl-1H-imidazol-4-yl)butyl]guanidine
• 英文别名: 2-Methylhomohistamine；3-(2-methyl-1H-imidazol-5-yl)propan-1-amine
• CAS: 112357-45-6
• 化学式: C₇H₁₃N₃
• mdl: MFCD09913079
• 分子量: 139.2
• InChiKey: IAQZZLBOHVMABT-UHFFFAOYSA-N

物化性质

• 沸点：
  352.5±25.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-cyano-1-methyl-3-[4-(2-methyl-1H-imidazol-4-yl)butyl]guanidine 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 1.25h， 生成 N-Benzoyl-N'-[3-(1H-imidazol-4-yl)-propyl]-N''-[3-(2-methyl-1H-imidazol-4-yl)-propyl]-guanidine
  参考文献：
  名称：

  Histamine analogues: imidazolylalkylguanidines, synthesis and in vitro pharmacology

  摘要：

  Impromidine analogues characterized by modified side chains connecting the guanidine and imidazole moieties have been prepared and tested for H-2-agonistic activity on isolated guinea-pig right atrium and for H-1-antagonistic activity on guinea-pig ileum, respectively. 3-(1H-Imidazol-4-yl)propylguanidines with varied cimetidine-like side chain (5a-d) proved to be almost full H-2-agonists and 5-70 times more potent than histamine, whereas compounds with beta- or gamma-methyl branched imidazolylpropyl moiety (5e, 5f, 5h) are only weak partial H-2-agonists. Both unsaturated impromidine analogues (5i, 5j) are full H-2-agonists, the (Z)-configurated compound 5j being about 4 times more potent than the (E)-configurated derivate 5i.

  DOI：

  10.1016/0223-5234(92)90056-7
• 作为产物：
  描述：

  5-(N-邻苯二甲酰亚氨基)-2-戊酮 在 盐酸 、 sodium hydroxide 、 氨 、 溴 作用下， 以 1,4-二氧六环 、 甲醇 、 正丁醇 为溶剂， 反应 35.0h， 生成 2-cyano-1-methyl-3-[4-(2-methyl-1H-imidazol-4-yl)butyl]guanidine
  参考文献：
  名称：

  Elz, Sigurd; Schunack, Walter, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1987, vol. 42, # 2, p. 238 - 242

  摘要：

  DOI：

文献信息

• Synthesis and Functional Characterization of Imbutamine Analogs as Histamine H₃and H₄Receptor Ligands
  作者：Roland Geyer、Melanie Kaske、Paul Baumeister、Armin Buschauer

  DOI：10.1002/ardp.201300316

  日期：2014.2

  EC50 = 59 nM, α = 0.8) was equipotent with imbutamine at the hH4R, but revealed about 16‐fold selectivity for the hH4R compared to the hH3R (EC50 980 nM, α = 0.36), whereas imbutamine preferred the hH3R. The functional activities were in agreement with radioligand binding data. The results support the hypothesis that, by analogy with histamine, methyl substitution in histamine homologs offers a way to shift the

  Imbutamine (4-(1H-imidazol-4-yl)butanamine) 是一种有效的组胺 H3 (H3R) 和 H4 受体 (H4R) 激动剂（EC50 值分别为 3 和 66 nM）。为了提高对 H4R 的选择性，伊布巴明中的咪唑环被甲基取代或被各种不同取代的杂环（1,2,3-三唑、1,2,4-三唑、吡啶、嘧啶）取代，作为潜在的生物电子等排体。使用表达相应人组胺受体亚型的 Sf9 昆虫细胞膜对 [35S]GTPγS 结合测定进行的研究表明，大多数合成的杂芳基烷基胺对两种受体仅具有非常微弱的活性。相比之下，在 4-咪唑基环上引入取代基对 H4R 选择性最有效。这适用于第 2 位的甲基取代，尤其是第 5 位的甲基取代。 5-甲基丁二胺 (H4R: EC50 = 59 nM, α = 0.8) 在 hH4R 上与伊姆布塔明等效，但与 hH3R 相比，hH4R 的选择性大约是 hH3R
• GAS TREATING SOLUTIONS CONTAINING IMIDAZOLE-AMINE COMPOUNDS
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ALABAMA

  公开号：US20180021723A1

  公开（公告）日：2018-01-25

  Systems comprising a composition where an imidazole is tethered to an amine and a solvent are described herein. Methods of their preparation and use are also described herein. The methods of using the systems include the reduction of volatile compounds from gas streams and liquid stream.

  本文描述了由咪唑与胺和溶剂相结合的组合物系统。同时也描述了它们的制备和使用方法。这些系统的使用方法包括从气流和液流中减少挥发性化合物的方法。
• Synthesis, SAR and selectivity of 2-acyl- and 2-cyano-1-hetarylalkyl-guanidines at the four histamine receptor subtypes: a bioisosteric approach
  作者：Roland Geyer、Patrick Igel、Melanie Kaske、Sigurd Elz、Armin Buschauer

  DOI：10.1039/c3md00245d

  日期：——

  In the search for potential bioisosteres of the 4-imidazolyl ring in acylguanidines (e.g. UR-AK24), known to possess affinity to several histamine receptor subtypes (HxR, x = 1–4), and cyanoguanidine-type H4R agonists (e.g. UR-PI376), the contribution of various heterocycles to agonism, antagonism and HR subtype selectivity was studied (recombinant human H1,2,3,4Rs, isolated guinea pig organs (H1R, H2R)). While minor structural modifications of UR-PI376 analogues were not tolerated regarding H4R agonism, in the case of the acylguanidines, a 1,2,4-triazole ring shifted the selectivity toward the H2R.

  在寻找酰基胍类（如 UR-AK24）（已知对几种组胺受体亚型（HxR，x = 1-4）具有亲和力）和氰基胍类 H4R 激动剂（如 UR-PI376）中 4-咪唑环的潜在生物异构体时，研究了各种杂环对激动作用、拮抗作用和 HR 亚型选择性的贡献（重组人 H1、2、3、4R，分离的胍类）。例如 UR-PI376），研究了各种杂环化合物对激动、拮抗和组胺受体亚型选择性的贡献（重组人 H1、2、3、4Rs，离体豚鼠器官（H1R、H2R））。UR-PI376类似物的微小结构改性对H4R的激动作用没有影响，而对酰基胍类化合物来说，1,2,4-三唑环会使其对H2R的选择性发生改变。
• ANTIOXIDANTS FOR PRODUCING LOW-EMISSION PUR SYSTEMS
  申请人：Evonik Degussa GmbH

  公开号：US20160264757A1

  公开（公告）日：2016-09-15

  A compound of the formula (I) in which R is CH 2 —CH(R I ), CH(R II )—CH(R II ), CH 2 —C(R II ) 2 , C(R II ) 2 —C(R II ) 2 , CH 2 —CH—CH 2 —R IV , C 6 H 6 —CH—CH 2 , C 6 H 6 —C(CH 3 )—CH 2 , where R I is C 2 to C 24 alkyl radical or alkene radical, R II is C 2 to C 24 alkyl radical or alkene radical, R III is C 3 to C 6 alkyl radical, which is arranged linearly, and R IV is OH, Cl, OCH 3 , OCH 2 —CH 3 , O—CH 2 —CH═CH 2 , O—CH═CH 2 molecule residue of epoxidized fats or oils, R 1 and R 2 independently of one another are C 1 -C 8 alkyl, cyclopentyl or cyclohexyl, especially tert-butyl, R 3 is an n-valent radical of C 1 -C 30 -alkyl, R 4 is hydrogen, an n-valent radical of C 1 -C 30 alkyl, which is optionally interrupted by one or more groups —NR 5 — or (where n=1-12) is an n-valent radical of C 5 -C 12 cycloalkyl, R 5 independently at each occurrence is hydrogen or methyl or —C q H 2q .

  化合物的化学式为（I），其中R为CH2—CH（RI），CH（RII）—CH（RII），CH2—C（RII）2，C（RII）2—C（RII）2，CH2—CH—CH2—RIV，C6H6—CH—CH2，C6H6—C（CH3）—CH2，其中RI为C2到C24烷基或烯基基团，RII为C2到C24烷基或烯基基团，RIII为线性排列的C3到C6烷基基团，RIV为OH，Cl，OCH3，OCH2—CH3，O—CH2—CH═CH2，O—CH═CH2环氧化脂肪酸或油的分子残基，R1和R2分别是C1-C8烷基，环戊基或环己基，尤其是叔丁基，R3是C1-C30烷基的n价基团，R4是氢，C1-C30烷基的n价基团，其可被一个或多个—NR5—或（其中n=1-12）的基团中断，R5在每次出现时独立地是氢或甲基或—CqH2q。
• POLYIMIDAZOLES FOR USE AS BILE ACID SEQUESTRANTS
  申请人：Lees Inez

  公开号：US20130189215A1

  公开（公告）日：2013-07-25

  The present invention provides crosslinked amine polymers effective for binding and removing bile salts from the gastrointestinal tract. These bile acid binding polymers or pharmaceutical compositions thereof can be administered to subjects to treat various conditions, including hypercholesteremia, diabetes, pruritus, irritable bowel syndrome-diarrhea (IBS-D), bile acid malabsorption, and the like.

  本发明提供了交联胺聚合物，可以有效地结合和清除胆汁酸从胃肠道中。这些胆酸结合聚合物或其制药组合物可以用于治疗各种疾病，包括高胆固醇血症，糖尿病，瘙痒，肠易激综合征-腹泻（IBS-D），胆酸吸收不良等。