{[氨基(亚氨基)甲基]氨基}乙酸盐酸盐 | 14901-20-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: {[氨基(亚氨基)甲基]氨基}乙酸盐酸盐
• 英文名称: guanidinoacetic acid hydrochloride
• 英文别名: glycocyamine hydrochloride；guanidineacetic acid hydrochloride；Carboxymethyl(diaminomethylidene)azanium;chloride；carboxymethyl(diaminomethylidene)azanium;chloride
• CAS: 14901-20-3
• 化学式: C₃H₇N₃O₂*ClH
• mdl: MFCD09800614
• 分子量: 153.568
• InChiKey: XXOMCDWWEZZWBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.13
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  3

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  {[氨基(亚氨基)甲基]氨基}乙酸盐酸盐 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Korndoerfer, Archiv der Pharmazie, 1904, vol. 242, p. 634

  摘要：

  DOI：
• 作为产物：
  描述：

  1H-吡唑-1-甲脒盐酸盐 、 聚甘氨酸 在 sodium carbonate 作用下， 反应 3.0h， 以77%的产率得到{[氨基(亚氨基)甲基]氨基}乙酸盐酸盐
  参考文献：
  名称：

  1H-Pyrazole-1-carboxamidine hydrochloride an attractive reagent for guanylation of amines and its application to peptide synthesis

  摘要：

  DOI：

  10.1021/jo00034a059
• 作为试剂：
  描述：

  N1,N5-双-Boc-亚精胺 在 palladium on activated charcoal 氢气 、 {[氨基(亚氨基)甲基]氨基}乙酸盐酸盐 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 55.0h， 生成 N¹-<<1-Methyl-4-(guanidinoacetamido)pyrrol-2-yl>carbonyl>-N⁴,N⁸-bis(tert-butoxycarbonyl)spermidine hydrochloride
  参考文献：
  名称：

  Synthesis, DNA binding and biological evaluation of synthetic precursors and novel analogs of netropsin

  摘要：

  A series of oligopeptides have been synthesized that are structurally related to the natural agent netropsin. The binding constants to double-stranded polynucleotides as well as the cytostatic activity against both murine human tumor cell lines and the in vitro activity against a range of DNA and RNA viruses have been determined for these novel compounds and some of their synthetic precursors. 1-Methyl-5-nitropyrrole-2-carboxylic acid methyl ester (4), N-[[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrol-2- yl]carbonyl]-L-alanine tert-butyl ester (28), and N-[[1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrol-2- yl]carbonyl]-L-alanyl-L-alanine tert-butyl ester (29) showed modest inhibitory effect on tumor cell proliferation (CD50 = 26-85 micrograms/mL). Of all the compounds that were evaluated, 28 proved the most potent antiviral agent. It was inhibitory to parainfluenza-3 virus and Coxsackie virus B4 in Vero cells at a concentration of 20 micrograms/mL.

  DOI：

  10.1021/jm00125a024

文献信息

• 6-[.alpha.-(.omega.-QUANIDINOALKANOYLAMIDO)ACYLAMIDO]PENICILLANIC ACIDS
  申请人：Pfizer Inc.

  公开号：US03933797A1

  公开（公告）日：1976-01-20

  6-[.alpha.-(.omega.-GUANIDINOALKANOYLAMIDO)ACYLAMIDO]PENICILLANIC ACIDS, THE NON-TOXIC SALTS AND ESTERS THEREOF ARE USEFUL AS ANTIBACTERIAL AGENTS, THERAPEUTIC AGENTS IN ANIMALS, INCLUDING MAN, OF PARTICULAR VALUE AGAINST GRAM-NEGATIVE BACTERIA, AND AS ANIMAL FEED NUTRITIONAL SUPPLEMENTS.

  6-[.alpha.-(.omega.-GUANIDINOALKANOYLAMIDO)ACYLAMIDO]PENICILLANIC ACIDS，其非毒性盐及酯在动物中，包括人类中，作为抗菌剂和治疗剂特别有效对抗革兰氏阴性细菌，并作为动物饲料营养补充剂。
• Structure–activity relationships of pyrrole amidine antiviral antibiotics III: Preparation of distamycin and congocidine derivatives based on 2,5-disubstituted pyrroles
  作者：Meir Bialer、Boris Yagen、Raphael Mechoulam、Yechiel Becker

  DOI：10.1002/jps.2600691125

  日期：1980.11

  of distamycin A and tripyrrole congocidine containing 2,5-disubstituted pyrroles were synthesized along with distamycin and congocidine homologs containing a single pyrrole ring. Selected compounds were evaluated for their cytotoxicity and antiviral activity. All of the tripyrrole derivatives tested in this series were nontoxic but were less active than distamycin A. The monopyrrole derivative, N-

  合成了含有2，5-二取代的吡咯的二霉素A和三吡咯刚果定的异构体，以及含有单个吡咯环的二霉素和刚果定同系物。评价所选化合物的细胞毒性和抗病毒活性。在该系列中测试的所有三吡咯衍生物均无毒，但活性比地西霉素A低。单吡咯衍生物N-甲基-5-硝基吡咯-2-羧酰胺基-β-丙ion盐酸盐无毒，且抗病毒活性几乎与地西霉素一样一种。
• Syntheses and Characterization of two cyclo‐pentazolate salts
  作者：Xieyang Wang、Zhen Dong、Rui Yang、Shengren Zhou、Zhiwen Ye

  DOI：10.1002/zaac.202000309

  日期：2021.3.26

  Two energetic salts of cyclo‐N5−, O‐methylisoure pentazolate (1) and guanidinoacetic acid pentazolate (2), were synthesized by metathesis reaction. All the energetic cyclo‐N5− salts were characterized by single‐crystal XRD, IR spectroscopy, 1H and 13C multinuclear NMR spectroscopy, thermal analysis (DSC) and elemental analysis. They exhibit good thermal stability with decomposition temperatures of

  的环-N二高能盐5 -，O- methylisoure pentazolate（1）和胍基乙酸pentazolate（2）中，通过复分解反应合成。所有的高能环-N 5 -通过单晶X射线衍射，IR光谱法，盐进行表征1 H和13 C ^多核NMR光谱学，热分析（DSC）和元素分析。它们表现出良好的热稳定性，分解温度超过100°C，并且与报道的非金属盐极为吻合。盐1还表现出很强的π-π相互作用。使用Gaussian 09和EXPLO5 v6.01程序计算这些盐的形成和爆炸性能的标准焓。化合物1和2的爆炸速度均为约7400m s -1，并且这两种盐表现出较低的机械敏感性（IS> 23 J，FS> 220 N）。因此，在这项工作中，新的戊唑盐的合成丰富了环戊唑盐体系，这有利于探索具有更高耐热性和更高爆震速度的戊唑盐。
• Structure-activity relationships of pyrrole amidine antiviral antibiotics. 2. Preparation of mono- and tripyrrole derivatives of congocidine
  作者：Meir Bialer、Boris Yagen、Raphael Mechoulam、Yechiel Becker

  DOI：10.1021/jm00184a018

  日期：1980.10

  virus (HSV) replication in cultured cells, and effects on the synthesis of HS DNA in isolated nuclei in vitro, as well as on DNA synthesis by purified HSV DNA polymerase. All synthesized tripyrrole derivatives of congocidine were less cytotoxic and more active than the parent drug in all the three ant iviral tests.

  合成了三种类型的刚果金（1）类似物的代表。测试了它们的细胞毒性，在培养细胞中对单纯疱疹病毒（HSV）复制的抑制以及对离体核中HS DNA合成的影响，以及纯化HSV DNA聚合酶对DNA合成的影响。在所有三个抗病毒试验中，所有合成的刚果金三吡咯衍生物的毒性都比母体药物小，活性更高。
• Structure elucidation of a condensation product of 4-aminopyrrole derivatives and dicyclohexylcarbodiimide
  作者：Meir Bialer、Boris Yagen、Raphael Mechoulam

  DOI：10.1002/jhet.5570170834

  日期：1980.12

  The chemical structure of the two condensation products of dicyclohexylcarbodiimide (DCC) with the precursors of the mono-pyrrole homologues of distamycin and with the mono and tri-pyrrole homologues of congocidine were established. The two products isolated were proven to be condensation products between 4-aminopyrrole derivatives and dicyclohexylcarbodiimide (DCC).

  建立了二环己基碳二亚胺（DCC）与二霉素单吡咯同系物的前体以及刚果金的单吡咯和三吡咯同系物的两个缩合产物的化学结构。分离出的两种产物被证明是4-氨基吡咯衍生物与二环己基碳二亚胺（DCC）之间的缩合产物。