N-苯基肼甲脒 | 53959-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苯基肼甲脒
• 英文名称: 1-Amino-3-phenyl-guanidine
• 英文别名: N-amino-N'-phenyl-guanidine；N-Amino-N'-phenyl-guanidin；1-Amino-3-phenyl-guanidin；N-phenylhydrazinecarboximidamide；1-amino-2-phenylguanidine
• CAS: 53959-11-8
• 化学式: C₇H₁₀N₄
• 分子量: 150.183
• InChiKey: RHXYLNBIHBDYLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.4
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  N-苯基肼甲脒 在 盐酸 、 sodium nitrite 作用下， 生成 莫非那
  参考文献：
  名称：

  Preparation and isomerization of 5-alkylaminotetrazoles

  摘要：

  DOI：

  10.1021/jo50013a002
• 作为产物：
  描述：

  苯基硫脲 在 一水合肼 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-苯基肼甲脒
  参考文献：
  名称：

  氨基胍Hy衍生物作为非肽NPFF1受体拮抗剂可逆阿片类药物引起的痛觉过敏。

  摘要：

  先前已显示神经肽FF受体（NPFF1R和NPFF2R）及其内源性配体神经肽FF具有抗阿片类药物的特性，并且在鸦片类药物长期服用相关的不良反应中起关键作用，包括阿片类药物引起的痛觉过敏和镇痛耐受性的发展。在这项工作中，我们试图通过将我们的注意力集中在一系列杂环上来鉴定新的NPFF受体配体，这些杂环作为刚性化的非肽NPFF受体配体，从已经描述的氨基胍（AGH）开始。结合实验和功能测定突出了用于体内实验的AGH 1n及其刚性化类似物2-氨基-二氢嘧啶22e。如先前使用原型二肽拮抗剂RF9所示，1n和22e均显着降低了芬太尼诱导的鼠持久性痛觉过敏。总而言之，这些数据表明，AGH硬化对两种NPFF受体均保持纳摩尔亲和力，同时改善了对NPFF1R的拮抗特性。

  DOI：

  10.1021/acschemneuro.8b00099

文献信息

• Synthesis, Antileishmanial Activity and in silico Studies of Aminoguanidine Hydrazones (AGH) and Thiosemicarbazones (TSC) Against Leishmania chagasi Amastigotes
  作者：Thiago M. de Aquino、Paulo H. B. França、Érica E. E. S. Rodrigues、Igor. J.S. Nascimento、Paulo F. S. Santos-Júnior、Pedro G. V. Aquino、Mariana S. Santos、Aline C. Queiroz、Morgana V. Araújo、Magna S. Alexandre-Moreira、Raiza R. L. Rodrigues、Klinger A. F. Rodrigues、Johnnatan D. Freitas、Jacques Bricard、Mario R. Meneghetti、Jean-Jacques Bourguignon、Martine Schmitt、Edeildo F. da Silva-Júnior、João X. de Araújo-Júnior

  DOI：10.2174/1573406417666210216154428

  日期：2022.2

  Leishmaniasis is a worldwide health problem, highly endemic in developing countries. Among the four main clinical forms of the disease, visceral leishmaniasis is the most severe, fatal in 95% of cases. The undesired side-effects from first-line chemotherapy and the reported drug resistance search for effective drugs that can replace or supplement those currently used an urgent need. Aminoguanidine hydrazones (AGH's) have been explored for exhibiting a diverse spectrum of biological activities, in particular the antileishmanial activity of MGBG. The bioisosteres thiosemicarbazones (TSC's) offer a similar biological activity diversity, including antiprotozoal effects against Leishmania species and Trypanosoma cruzi.

  Considering the impact of leishmaniasis worldwide, this work aimed to design, synthesize, and perform a screening upon L. chagasi amastigotes and for the cytotoxicity of the small "in-house" library of both AGH and TSC derivatives and their structurally-related compounds.

  A set of AGH's (3-7), TSC's (9, 10), and semicarbazones (11) were initially synthesized. Subsequently, different semi-constrained analogs were designed and also prepared, including thiazolidines (12), dihydrothiazines (13), imidazolines (15), pyrimidines (16, 18) azines (19, 20), and benzotriazepinones (23-25). All intermediates and target compounds were obtained with satisfactory yields and exhibited spectral data consistent with their structures. All final compounds were evaluated against L. chagasi amastigotes and J774.A1 cell line. Molecular docking was performed towards trypanothione reductase using GOLD® software.

  The AGH's 3i, 4a, and 5d, and the TSC's 9i, 9k, and 9o were selected as valuable hits. These compounds presented antileishmanial activity compared with pentamidine, showing IC50 values ranged from 0.6 to 7.27 μM, maximal effects up to 55.3%, and satisfactory SI values (ranged from 11 to 87). On the other hand, most of the resulting semi-constrained analogs were found cytotoxic or presented reduced antileishmanial activity. In general, TSC class is more promising than its isosteric AGH analogs, and the beneficial aromatic substituent effects are not similar in both series. In silico studies have suggested that these hits are capable of inhibiting the trypanothione reductase from the amastigote forms.

  The promising antileishmanial activity of three AGH’s and three TSC’s was characterized. These compounds presented antileishmanial activity compared with PTD, showing IC50 values ranged from 0.6 to 7.27 μM, and satisfactory SI values. Further pharmacological assays involving other Leishmania strains are under progress, which will help to choose the best hits for in vivo experiments.

  背景：利什曼病是全球性健康问题，在发展中国家高度流行。在该病的四种主要临床形式中，内脏利什曼病是最严重的，95%的病例会致命。由于一线化疗药物的不良副作用和报道的药物耐药性，迫切需要寻找可以替代或补充当前使用的有效药物。氨基胍脒肼酮（AGH）已被探索用于展示多样的生物活性，特别是MGBG的抗利什曼病活性。生物同功异构体硫脲半胱氨酮（TSC）提供类似的生物活性多样性，包括对利什曼病和克氏锥虫的抗原虫效应。 目的：考虑到利什曼病在全球范围内的影响，本研究旨在设计、合成并对L. chagasi阿马斯蒂果虫进行筛选，以及对小型“内部”AGH和TSC衍生物及其结构相关化合物的细胞毒性进行评估。 方法：首先合成了一组AGH（3-7）、TSC（9, 10）和半胱氨酮（11）。随后，设计并制备了不同的半约束类似物，包括噻唑烷（12）、二氢噻嗪（13）、咪唑烷（15）、嘧啶（16, 18）、吲哚烷（19, 20）和苯并三唑环酮（23-25）。所有中间体和目标化合物均以满意的收率获得，并展示了与其结构一致的光谱数据。所有最终化合物均对L. chagasi阿马斯蒂果虫和J774.A1细胞系进行了评估。使用GOLD®软件对其进行了针对巯基还原酶的分子对接。 结果：AGH的3i、4a和5d以及TSC的9i、9k和9o被选为有价值的命中物。这些化合物与五环胺相比具有抗利什曼病活性，IC50值范围从0.6到7.27μM，最大效果高达55.3％，满意的SI值（范围从11到87）。另一方面，大多数结果的半约束类似物被发现具有细胞毒性或具有降低的抗利什曼病活性。总体而言，TSC类比其同功异构AGH类更有前景，而有益的芳香族取代作用在两个系列中并不相似。计算机模拟研究表明这些命中物能够抑制阿马斯蒂果虫的巯基还原酶。 结论：三种AGH和三种TSC的有前景的抗利什曼病活性得到了表征。这些化合物与PTD相比具有抗利什曼病活性，IC50值范围从0.6到7.27μM，SI值满意。正在进行涉及其他利什曼病菌株的进一步药理学评估，这将有助于选择最佳的命中物进行体内实验。
• Rubber composition
  申请人：BRIDGESTONE CORPORATION, OTSUKA CHEMICAL CO., LTD.

  公开号：US20030134947A1

  公开（公告）日：2003-07-17

  Provided is a rubber composition comprising 100 parts by weight of a rubber component comprising at least one selected from the group consisting of natural rubber and synthetic rubbers and 0.05 to 20 parts by weight of at least one selected from compounds (A) represented by the following Formula (I): 1 wherein A 1 and A 2 each represent R—, R—NH—, R—X—NH—, R—NH—NH— or R—X—NH—NH—, and A 1 and A 2 may be the same or different; R represents any one of a hydrogen atom, an alkyl group having 1 to 18 carbon atoms which may be branched, a cycloalkyl group, an aryl group, an alkylaryl group or an alkenyl group, each group of which may include at least one substituent containing a sulfur atom, a nitrogen atom and an oxygen atom, and two R's may be combined in a molecule to form a ring containing a >C═NH bond; and X represents any one of those shown below: 2

  提供的是一种橡胶组合物，包括100份重量的橡胶组分，其中至少包括天然橡胶和合成橡胶中的一种，并且还包括0.05至20份重量的至少一种选择自以下式(I)所表示的化合物(A)：1其中，A1和A2分别表示R—，R—NH—，R—X—NH—，R—NH—NH—或R—X—NH—NH—，且A1和A2可以相同也可以不同；R表示氢原子、含有1至18个碳原子的烷基，可以是支链的，环烷基，芳基，烷基芳基或烯基，每个基中都可以包含至少一个含有硫原子、氮原子和氧原子的取代基，两个R可以结合在分子中形成一个含有>C═NH键的环；X表示下列任意一种：2
• Heat ageing resistant rubber composition
  申请人：Bridgestone Corporation

  公开号：EP1101793A1

  公开（公告）日：2001-05-23

  Provided is a rubber composition comprising 100 parts by weight of a rubber component comprising at least one selected from the group consisting of natural rubber and synthetic rubbers and 0.05 to 20 parts by weight of at least one selected from compounds (A) represented by the following Formula (I): wherein A1 and A2 each represent R-, R-NH-, R-X-NH-, R-NH-NH- or R-X-NH-NH-, and A1 and A2 may be the same or different; R represents any one of a hydrogen atom, an alkyl group having 1 to 18 carbon atoms which may be branched, a cycloalkyl group, an aryl group, an alkylaryl group or an alkenyl group, each group of which may include at least one substituent containing a sulfur atom, a nitrogen atom and an oxygen atom, and two R's may be combined in a molecule to form a ring containing a >C=NH bond; and X represents any one of those shown below:

  本发明提供了一种橡胶组合物，该组合物包含按重量计 100 份的橡胶成分，其中至少包含一种选自天然橡胶和合成橡胶组成的组的橡胶成分，以及按重量计 0.05 至 20 份的至少一种选自下式 (I) 所代表化合物 (A) 的橡胶成分： 其中 A1 和 A2 各自代表 R-、R-NH-、R-X-NH-、R-NH-NH- 或 R-X-NH-NH-，A1 和 A2 可以相同或不同；R 代表氢原子、具有 1 至 18 个碳原子且可以是支链的烷基、环烷基、芳基、烷芳基或烯基的任一种，其中每个基团可包括至少一个含有硫原子、氮原子和氧原子的取代基，两个 R 可在分子中结合形成一个含有 >C=NH 键的环；X 代表下表中的任一种：
• Petersen et al., Angewandte Chemie, 1955, vol. 67, p. 217,219
  作者：Petersen et al.

  DOI：——

  日期：——
• Werbel; Hung; McNamara, European Journal of Medicinal Chemistry, 1985, vol. 20, # 4, p. 363 - 370
  作者：Werbel、Hung、McNamara、Ortwine

  DOI：——

  日期：——