N-(4-phenylbutyl)guanidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-phenylbutyl)guanidine
• 英文别名: 1-(4-Phenylbutyl)guanidine；2-(4-phenylbutyl)guanidine
• 化学式: C₁₁H₁₇N₃
• mdl: MFCD20545851
• 分子量: 191.276
• InChiKey: MMNBVOHENPBWSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-phenylbutyl)guanidine 、 3,5-二氨基-6-氯吡嗪-2-羧酸甲酯 以 甲醇 为溶剂， 反应 2.0h， 生成 benzamil
  参考文献：
  名称：

  生产新的阿米洛利作为线粒体呼吸道复合物I的有效抑制剂。

  摘要：

  Amilorides，Na（+）/ H（+）反转运蛋白的著名抑制剂，也显示出抑制细菌和线粒体NADH-醌氧化还原酶（复合体I）的作用。由于牛线粒体复合体I的膜亚基ND2，ND4和ND5与Na（+）/ H（+）反转运蛋白同源，因此阿米洛利被认为与任何或所有反转运蛋白样亚基结合；但是，没有直接的实验证据支持这一观点。光亲和标记法是鉴定牛复合物I中阿米洛利结合位点的有力技术。商业上可获得的阿米洛利，例如5-（N-乙基-N-异丙基）阿米洛利，由于其结合力低，因此不适合用作合成光反应性阿米洛利的设计模板。对牛复合体I的亲和力。因此，我们试图修改市售阿米洛利的结构，以获得更有效的衍生物。我们成功地生产了两个光反应性阿米洛利（PRA1和PRA2），在分子的相对末端具有一个对光不稳定的叠氮基团。

  DOI：

  10.1080/09168451.2015.1010479
• 作为产物：
  描述：

  苯基-4-丁胺 在 sodium methylate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 2.5h， 生成 N-(4-phenylbutyl)guanidine
  参考文献：
  名称：

  生产新的阿米洛利作为线粒体呼吸道复合物I的有效抑制剂。

  摘要：

  Amilorides，Na（+）/ H（+）反转运蛋白的著名抑制剂，也显示出抑制细菌和线粒体NADH-醌氧化还原酶（复合体I）的作用。由于牛线粒体复合体I的膜亚基ND2，ND4和ND5与Na（+）/ H（+）反转运蛋白同源，因此阿米洛利被认为与任何或所有反转运蛋白样亚基结合；但是，没有直接的实验证据支持这一观点。光亲和标记法是鉴定牛复合物I中阿米洛利结合位点的有力技术。商业上可获得的阿米洛利，例如5-（N-乙基-N-异丙基）阿米洛利，由于其结合力低，因此不适合用作合成光反应性阿米洛利的设计模板。对牛复合体I的亲和力。因此，我们试图修改市售阿米洛利的结构，以获得更有效的衍生物。我们成功地生产了两个光反应性阿米洛利（PRA1和PRA2），在分子的相对末端具有一个对光不稳定的叠氮基团。

  DOI：

  10.1080/09168451.2015.1010479

文献信息

• Fluorescence tagging of glycans and other biomolecules through reductive amination for enhanced MS signals
  申请人：WATERS TECHNOLOGIES CORPORATION

  公开号：US11061023B2

  公开（公告）日：2021-07-13

  Novel reagents comprising MS active, fluorescent compounds having an activated functionality for reaction with aldehydes and useful in labeling biomolecules such as glycans and methods of making the same are taught and described.

  本文教导并描述了由 MS 活性荧光化合物组成的新型试剂，该化合物具有与醛反应的活化官能团，可用于标记生物大分子（如聚糖），并介绍了制作该试剂的方法。
• Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals
  申请人：Waters Technologies Corporation

  公开号：US11352325B2

  公开（公告）日：2022-06-07

  Reagents comprising MS active, fluorescent molecules with an activated functionality for reaction with amines useful in tagging biomolecules such as N-glycans and uses thereof are taught and described. In particular embodiments, the MS active, fluorescent molecules are of the compound of the Formula III or of the Formula IV where R1, R2 and R3 are defined herein.

  本文教导并描述了包含 MS 活性荧光分子的试剂，这些分子具有活化功能，可与胺反应，用于标记 N-聚糖等生物大分子及其用途。在特定的实施方案中，MS 活性荧光分子是式 III 的化合物 或式 IV 其中 R1、R2 和 R3 在此定义。
• Methods of enhancing MS detection of tagged glycans
  申请人：WATERS TECHNOLOGIES CORPORATION

  公开号：US11353461B2

  公开（公告）日：2022-06-07

  Methods for derivatization of biomolecules including glycans or other biopolymers with one or more fluorescent, MS active compounds by reductive amination or rapid tagging in order to produce derivatized glycan having a pKa>7 and between about 200 Å2 and about 1000 Å2 of nonpolar surface area are described.

  本研究描述了通过还原胺化或快速标记的方法，用一种或多种荧光质谱活性化合物对生物大分子（包括聚糖或其他生物聚合物）进行衍生，以产生 pKa>7 且非极性表面积在约 200 Å2 到约 1000 Å2 之间的衍生聚糖。
• Potent Inhibition of NTPase/Helicase of the West Nile Virus by Ring-Expanded (“Fat”) Nucleoside Analogues
  作者：Ning Zhang、Huan-Ming Chen、Verena Koch、Herbert Schmitz、Michal Minczuk、Piotr Stepien、Ali I. Fattom、Robert B. Naso、Kishna Kalicharran、Peter Borowski、Ramachandra S. Hosmane

  DOI：10.1021/jm030277k

  日期：2003.10.1

  A series of ring-expanded ("fat") nucleoside analogues (RENs) containing the 6-aminoimidazo-[4,5-e] [1,3]diazepine-4,8-dione ring system have been synthesized and screened for inhibition of NTPase/helicase of the West Nile Virus (WNV). To assess the selectivity of RENs against the viral enzymes, a truncated form of human enzyme Suv3((Delta1-159)) was also included in the study. Ring-expanded nucleosides 16, 17, and 19, which possess the long C-12, C-14, and C-18 side-chains, respectively, at position 6, as well as the ring-expanded heterocycle 39, which contains aralkyl substitution at position 1, were all found to have excellent profiles of activity and selectivity toward the viral versus human enzymes against the West Nile Virus (IC50 ranging 1-10 muM). Compound 30, while being an equally potent inhibitor of WNV, was found to be somewhat less selective, whereas compound 36, which is an alpha-anomeric counterpart of 30, exhibited potent and selective inhibition of WN-V (IC50 1-3 muM). The same compounds that showed potent inhibition of viral helicase activity completely failed to show any activity against the viral NTPase reaction even up to 500 muM. However, at concentrations >500 muM of RENs and the ATP concentrations >10 times the K-m value of the enzyme, a significant activation of NTPase activity was observed. This activating effect underwent further dramatic enhancement (>1000%) by further increases in ATP concentration in the reaction mixture, suggesting that the viral helicase and NTPase reactions are not coupled. A tentative mechanistic model has been proposed to explain the observed results.
• Direct Guanylation of Amino Groups by Cyanamide in Water: Catalytic Generation and Activation of Unsubstituted Carbodiimide by Scandium(III) Triflate
  作者：Katsunori Tanaka、Kazuki Tsubokura、Takayuki Iwata、Misako Taichi、Almira Kurbangalieva、Koichi Fukase、Yoichi Nakao

  DOI：10.1055/s-0033-1341080

  日期：——

  Guanylation proceeded efficiently upon treatment of the various amines with cyanamide in the presence of catalytic amounts of scandium(III) triflate under mild conditions. The method did not require the guanylation reagents to be preactivated, and the reaction proceeded efficiently in water. The method, therefore, has practical utility for substrates that dissolve only in aqueous solutions, for example, peptides or pharmacologically important compounds.