1-trityl-4-(4-aminobutyl)imidazole | 195053-83-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-trityl-4-(4-aminobutyl)imidazole
• 英文别名: 4-(1-trityl-1H-imidazol-4-yl)butan-1-amine；4-(4-aminobutyl)-1-(triphenylmethyl)-imidazole；4-(1-tritylimidazol-4-yl)butan-1-amine
• CAS: 195053-83-9
• 化学式: C₂₆H₂₇N₃
• 分子量: 381.52
• InChiKey: XFLDWPMCZYJVJC-UHFFFAOYSA-N

物化性质

• 沸点：
  545.2±38.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-trityl-4-(4-aminobutyl)imidazole 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 Propane-2-sulfonic acid [4-(1H-imidazol-4-yl)-butyl]-amide; hydrochloride
  参考文献：
  名称：

  Novel H3 receptor antagonists. Sulfonamide homologs of histamine

  摘要：

  Sulfonamides derived from 4(5)-(omega-aminoalkyl)-1H-imidazoles containing chain lengths of three- to five-carbons were synthesized. Good to moderate H-3 receptor binding affinities were observed for several butyl and pentyl homologs, whereas binding affinities were considerably weaker in the propyl series. Separation of the imidazole ring and the sulfonamide unit by a four- or five-carbon tether afforded potent H-3 receptor antagonists. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00379-5
• 作为产物：
  描述：

  2-[(E)-4-(1-tritylimidazol-4-yl)but-3-enyl]isoindole-1,3-dione 在 palladium on activated charcoal 氢气 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 80.0 ℃ 、310.27 kPa 条件下， 反应 4.0h， 生成 1-trityl-4-(4-aminobutyl)imidazole
  参考文献：
  名称：

  Novel H3 receptor antagonists. Sulfonamide homologs of histamine

  摘要：

  Sulfonamides derived from 4(5)-(omega-aminoalkyl)-1H-imidazoles containing chain lengths of three- to five-carbons were synthesized. Good to moderate H-3 receptor binding affinities were observed for several butyl and pentyl homologs, whereas binding affinities were considerably weaker in the propyl series. Separation of the imidazole ring and the sulfonamide unit by a four- or five-carbon tether afforded potent H-3 receptor antagonists. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00379-5

文献信息

• UR-DEBa242: A Py-5-Labeled Fluorescent Multipurpose Probe for Investigations on the Histamine H₃ and H₄ Receptors
  作者：Edith Bartole、Lukas Grätz、Timo Littmann、David Wifling、Ulla Seibel、Armin Buschauer、Günther Bernhardt

  DOI：10.1021/acs.jmedchem.0c00160

  日期：2020.5.28

  fluorescent probes for the histamine H3 receptor (H3R) and especially for the H4R orthologs [e.g., human (h) and mouse (m)] are highly needed as versatile complementary tools to radioligands. In view of fluorescent probes for BRET-based binding studies and for localizing the H4R in live cells, we synthesized and biologically characterized Py-5-labeled histamine derivatives. The most notable compound

  非常需要用于组胺H3受体（H3R）尤其是H4R直系同源物[例如人（h）和小鼠（m）]的具有全面特征的荧光探针，作为放射性配体的通用补充工具。鉴于荧光探针用于基于BRET的结合研究和在活细胞中定位H4R，我们合成了Py-5标记的组胺衍生物并对其进行了生物学表征。最著名的化合物是UR-DEBa242（26，1- [4-（1H-咪唑-4-基）丁基] -4-（1E，3E）-4- [4-（二甲基氨基）苯基] buta-1 ，3-二烯基} -2,6-二甲基吡啶氢三氟乙酸盐三氟乙酸盐），在hH3R [pEC50（报告基因）8.77]上起部分激动剂的作用，在h / mH4Rs [pIC50（报告基因）8.76]上起反向激动剂/拮抗剂的作用。 /7.08; pIC50 / pKb（β-arrestin2）7.81 / 7.30]。在共聚焦显微镜下 26个被证明适合在活细胞中进行hH4R定位和运输研究。在NLuc-hH3
• Sulfonamides and sulfamides as H.sub.3 receptor antagonists
  申请人：James Black Foundation Limited

  公开号：US06080871A1

  公开（公告）日：2000-06-27

  Compounds of formula (I) or (II) wherein R.sup.1 is C.sub.4 to C.sub.20 hydrocarbyl (in which one or more hydrogen atoms may be replaced by halogen, and up to three carbon atoms may be replaced by oxygen, nitrogen or sulphur atoms, provided that R.sup.1 does not contain an --O--O-- group), R.sup.2 is H or C.sub.1 to C.sub.3 alkyl, m is from 1 to 15, n is from 2 to 6, each X group is independently (a), or one X group is --N(R.sup.4)--, --O-- or --S-- and the remaining X groups are independently (a), wherein R.sup.3 is H, C.sub.1 to C.sub.6 alkyl, --CO.sub.2 R.sup.5, --CONR.sup.5.sub.2, --CR.sup.5.sub.2 OR.sup.6 or --OR.sup.5 (in which R.sup.5 and R.sup.6 are H or C.sub.1 to C.sub.3 alkyl), and R.sup.4 is H or C.sub.1 to C.sub.6 alkyl, each Y group is independently --C(R.sup.3)R.sup.4 --, or up to two Y groups are --N(R.sup.4)--, --O-- or --S-- and the remaining Y groups are independently --C(R.sup.3)R.sup.4 --, wherein R.sup.3 is as defined above, one R.sup.4 group in the structure is imidazoyl or imidazoylalkyl and the remaining R.sup.4 groups are H or C.sub.1 to C.sub.6 alkyl, and Z is >C(R.sup.7)NR.sup.2 -- or >N--, wherein R.sup.7 is any of the groups recited above for R.sup.3, and pharmaceutically acceptable salts thereof are ligands at histamine H.sub.3 receptors. ##STR1##

  式(I)或(II)的化合物，其中R.sup.1为C.sub.4至C.sub.20的烃基（其中一个或多个氢原子可以被卤素取代，最多三个碳原子可以被氧、氮或硫原子取代，前提是R.sup.1不含有--O--O--基团），R.sup.2为H或C.sub.1至C.sub.3的烷基，m为1至15，n为2至6，每个X基团独立地为(a)，或一个X基团为--N(R.sup.4)--，--O--或--S--，其余的X基团独立地为(a)，其中R.sup.3为H，C.sub.1至C.sub.6的烷基，--CO.sub.2R.sup.5，--CONR.sup.5.sub.2，--CR.sup.5.sub.2OR.sup.6或--OR.sup.5（其中R.sup.5和R.sup.6为H或C.sub.1至C.sub.3的烷基），而R.sup.4为H或C.sub.1至C.sub.6的烷基，每个Y基团独立地为--C(R.sup.3)R.sup.4--，或最多两个Y基团为--N(R.sup.4)--，--O--或--S--，其余的Y基团独立地为--C(R.sup.3)R.sup.4--，其中R.sup.3如上定义，结构中的一个R.sup.4基团为咪唑基或咪唑基烷基，其余的R.sup.4基团为H或C.sub.1至C.sub.6的烷基，Z为>C(R.sup.7)NR.sup.2--或>N--，其中R.sup.7为R.sup.3中上述所述的任一基团，以及其药学上可接受的盐是组成组织胺H.sub.3受体的配体。
• Identification of a dual histamine H1/H3 receptor ligand based on the H1 antagonist chlorpheniramine
  作者：Robert Aslanian、Mwangi wa Mutahi、Neng-Yang Shih、John J. Piwinski、Robert West、Shirley M. Williams、Susan She、Ren-Long Wu、John A. Hey

  DOI：10.1016/s0960-894x(03)00357-3

  日期：2003.6

  Combining the first generation H, antihistamine chlorpheniramine (1) with H-3 ligands of the alkylamine type has led to the identification of compound 9d, a dual ligand of both the H-1 and H-3 receptors. (C) 2003 Elsevier Science Ltd. All rights reserved.
• HISTAMINE H 3 RECEPTOR LIGANDS
  申请人：JAMES BLACK FOUNDATION LIMITED

  公开号：EP0882023B1

  公开（公告）日：2003-06-04
• SUBSTITUTED IMIDAZOLES AS DUAL HISTAMINE H1 AND H3 AGONISTS OR ANTAGONISTS
  申请人：Schering Corporation

  公开号：EP1318993B1

  公开（公告）日：2008-08-20