N-1-(pyrid-2-yl)butane-1,4-diamine | 92992-91-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-1-(pyrid-2-yl)butane-1,4-diamine
• 英文别名: N-(2-pyridyl)-1,4-diaminobutane；2-(N-(4-aminobut-1-yl)amino)pyridine；2-(4-amino-butylamino)-pyridine；2-[(4-Amino-1-butyl)amino]pyridine；N-(2-pyridyl)butylenediamine；N-(4-aminobutyl)pyridin-2-amine；N'-pyridin-2-ylbutane-1,4-diamine
• CAS: 92992-91-1
• 化学式: C₉H₁₅N₃
• mdl: MFCD11869077
• 分子量: 165.238
• InChiKey: RAJSAPSERUGCBT-UHFFFAOYSA-N

物化性质

• 沸点：
  323.4±22.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-1-(pyrid-2-yl)butane-1,4-diamine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-(4-(N-(3,4-Dichlorobenzyl)-N-(pyridin-2-yl)amino)butyl)-3-(3-(imidazol-1-yl)propyl)thiourea
  参考文献：
  名称：

  Nonpeptide Somatostatin Agonists with sst₄ Selectivity:  Synthesis and Structure−Activity Relationships of Thioureas

  摘要：

  Utilizing NNC 26-9100 (11) as a structural lead, a variety of nonpeptide derivatives of somatostatin were synthesized and evaluated for sst(2) and sst(4) receptor binding affinity. A novel thiourea scaffold was utilized to attach (1) a heteroaromatic nucleus to mimic the Trp(8) residue, (2) a nonheteroaromatic nucleus to mimic Phe(7), and (3) a primary amine or other basic group to mimic the Lys(9) residue of somatostatin. Displacement studies were carried out using membranes from cell lines expressing ssts [BHK cells (sst(4)) and HEK 293 cells (sst(2))] utilizing [I-125]Tyr(11)-SRIF as the radioligand. Several thioureas (11, 38, 39, 41, and 42) and the urea 66 exhibited K-i values of less than 100 nM. The thioureas 11 (K-i = 6 nM) and 41 (K-i = 16 nM) and the urea 66 (K-i = 14 nM) are believed to be the most potent nonpeptide sst(4) agonists known. Since the thiourea 11 and the urea 66 exhibit high ssts selectivity, these novel nonpeptide derivatives may be useful tools for studying the sst(4) receptor. Studies are currently in progress to evaluate the therapeutic potential of NNC 26-9100 (11) in the treatment of glaucoma.

  DOI：

  10.1021/jm980118e
• 作为产物：
  描述：

  2-氯吡啶 、 四亚甲基二胺 在 吡啶 作用下， 反应 0.5h， 生成 N-1-(pyrid-2-yl)butane-1,4-diamine
  参考文献：
  名称：

  作为组胺 H3 和 H4 受体配体的烟酰胺类似物的合成和功能表征

  摘要：

  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

  DOI：

  10.1002/ardp.201300316

文献信息

• 2-Pyridylaminoakylamino-4-pyrimidones useful as histamine H.sub.1
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04547506A1

  公开（公告）日：1985-10-15

  Pyridine derivatives are disclosed which are useful as histamine H.sub.1 -antagonists.

  已披露了作为组胺H.sub.1-拮抗剂有用的吡啶衍生物。
• 2-(2-Pyridylaminoalkylamino)-4-pyrimidones
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04532246A1

  公开（公告）日：1985-07-30

  Pyridine derivatives are disclosed which are useful as histamine H.sub.1 -antagonists.

  吡啶衍生物被披露，可用作组胺H.sub.1-拮抗剂。
• Amine Modification of Digested Peptide at C-Terminal End during Protein Digestion by Protease
  作者：Toshiyuki Ito、Yoshiaki Sugita、Koichi Takao、Yoshihiko Ikeguchi、Akira Shirahata

  DOI：10.1248/bpb.30.1838

  日期：——

  We recently reported that C-terminal polyamine modification occurs when proteins are digested with trypsin in the presence of polyamine [Biochem. Biophys. Res. Commun., 356, 159—162 (2007)]. In the present study, the characteristics of this C-terminal modification in the presence of protease and amine were investigated. When hemoglobin (HB) was digested with trypsin in the presence of N-(2-pyridyl)-1,4-diaminobutane (Py4), formation of the modified peptide was dependent on time and on HB or Py4 concentration. When synthetic peptide was treated with trypsin in the presence of Py4, ca. 0.1% of the peptide was modified with Py4. When HB or cytochrome C was treated with a range of serine proteases in the presence of various amines (Py4, N-(2-pyridyl)-1,3-diaminopropane, tranexamic acid, isonicotinic acid hydrazide and ampicillin), the modified peptide was detected in all cases tested, thus suggesting that amine modification widely accompanies digestion by proteases.

  我们最近报告了在存在多胺的情况下，蛋白质在胰蛋白酶消化时会发生C末端多胺修饰[生物化学与生物物理研究通讯，356，159—162（2007）]。在本研究中，探讨了在存在蛋白酶和胺时这种C末端修饰的特征。当将血红蛋白（HB）与胰蛋白酶在存在N-(2-吡啶基)-1,4-二氨基丁烷（Py4）的情况下消化时，修饰肽的形成依赖于时间和HB或Py4的浓度。当合成肽在Py4存在的情况下与胰蛋白酶处理时，约0.1%的肽被Py4修饰。当HB或细胞色素C在多种胺（Py4，N-(2-吡啶基)-1,3-二氨基丙烷，氨甲环酸，异烟酸肼和青霉素）存在的情况下与一系列丝氨酸蛋白酶处理时，在所有测试的情况下均检测到修饰肽，这表明胺修饰广泛伴随蛋白酶的消化。
• 3-Pyridylaminoalkyleneamino-4-amino-1,2,5-thiadiazole-1-oxides,
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04692456A1

  公开（公告）日：1987-09-08

  New 3,4-diamino-1,2,5-thiadiazole oxide derivatives which are histamine H.sub.1 -antagonists. A specific compound of this invention is 3-[3-(N-propyl-N-2-pyridylamino)-propylamino]-4-(4-pyridylmethyl)amino-1,2 ,5-thiadiazole-1-oxide.

  新的3,4-二氨基-1,2,5-噻二唑氧化物衍生物，它们是组胺H.sub.1-拮抗剂。该发明的一种特定化合物是3-[3-(N-丙基-N-2-吡啶基氨基)-丙基氨基]-4-(4-吡啶甲基)氨基-1,2,5-噻二唑-1-氧化物。
• 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。