1-硝基脒基-3,5-二甲基-吡唑 | 2946-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-硝基脒基-3,5-二甲基-吡唑
• 英文名称: 3,5-dimethyl-N-nitro-1-pyrazole-1-carboxamidine
• 英文别名: 3,5-dimethyl-N-nitro-1H-pyrazole-1-carboxamidine；3,5-dimethyl-N'-nitro-1H-pyrazole-1-carboximidamide；1H-Pyrazole-1-carboximidamide, 3,5-dimethyl-N-nitro-；3,5-dimethyl-N-nitropyrazole-1-carboximidamide
• CAS: 2946-89-6
• 化学式: C₆H₉N₅O₂
• mdl: MFCD00707522
• 分子量: 183.17
• InChiKey: YJQYMUPERFRTJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  1-硝基脒基-3,5-二甲基-吡唑 在 硫酸 、 硝酸 作用下， 生成 3,5-二甲基-4-硝基吡唑
  参考文献：
  名称：

  Studies in the Pyrazole Series. II. The 1-Nitroguanyl Type

  摘要：

  DOI：

  10.1021/ja01102a009
• 作为产物：
  描述：

  乙酰丙酮 、 1-氨基-3-硝基胍 在 溶剂黄146 作用下， 反应 7.0h， 以80%的产率得到1-硝基脒基-3,5-二甲基-吡唑
  参考文献：
  名称：

  3,5-二甲基-N-硝基-1H-吡唑-1-甲脒优化氨基胍合成胍

  摘要：

  用于制备胍类的有用试剂 3,5-二甲基-N-硝基-1-吡唑-1-甲脒 (DMNPC) 的合成已得到优化。描述了使用该试剂通过硝基胍以纯形式制备一系列胍的详细协议。已经对 DMNPC 和胍基化试剂 N,N'-bis-Boc-1-pyrazole-1-carboxamidine (2) 和 N,N'-bis-Boc-N'-triflylguanidine (3) 的效率进行了比较。

  DOI：

  10.1055/s-2004-829130

文献信息

• CXCR4 chemokine receptor binding comounds
  申请人：——

  公开号：US20040209921A1

  公开（公告）日：2004-10-21

  The present invention relates to compounds that bind to chemokine receptors, and having the formula 1 wherein each A, X, Y, R 1 , R 2 and R 3 are substituents. The present invention also relates to methods of using such compounds, such as in treating HIV infection and inflammatory conditions such as rheumatoid arthritis. Furthermore, the present invention relates to methods to elevate progenitor and stem cell counts, as well as methods to elevate white blood cell counts, using such compounds.

  本发明涉及与趋化因子受体结合的化合物，其具有式1的结构，其中A、X、Y、R1、R2和R3均为取代基。本发明还涉及使用这类化合物的方法，例如在治疗HIV感染和炎症性疾病如类风湿性关节炎中的应用。此外，本发明还涉及使用这类化合物来提高祖细胞和干细胞计数的方法，以及提高白细胞计数的方法。
• NOVEL IMIDAZOLE DERIVATIVES, PREPARATION AND USER THEREOF AS MEDICINE
  申请人：Liberatore Anne-Marie

  公开号：US20090186930A1

  公开（公告）日：2009-07-23

  The invention concerns novel imidazole derivatives of general formula (I), wherein Z′ and Z represent different variable groups. Said products have an antitumoral activity. The invention also concerns pharmaceutical compositions containing said products and their use for preparing antitumoral medicine.

  该发明涉及一种通式(I)的新型咪唑衍生物，其中Z′和Z代表不同的变量基团。所述产品具有抗肿瘤活性。该发明还涉及含有所述产品的药物组合物以及它们用于制备抗肿瘤药物的用途。
• Protecting-group strategies for the synthesis of N  4-substituted and N  1,N  8-disubstituted spermidines, exemplified by hirudonine
  作者：Bernard T. Golding、Andrew Mitchinson、William Clegg、Mark R. J. Elsegood、Roger J. Griffin

  DOI：10.1039/a806355i

  日期：——

  Methods are described for the preparation of derivatives of the polyamines 1,4-diaminobutane (putrescine) and N-(3-aminopropyl)-1,4-diaminobutane (spermidine) in which a particular amino group is modified with, e.g., a guanidino function. Specific amino groups in these polyamines were protected as N-trifluoroacetyl and N-4-azidobenzyloxycarbonyl derivatives, which were unmasked chemoselectively using methanolic ammonia and dithiothreitol–triethylamine, respectively. Guanidino functions were introduced by an improved procedure in which an amino group was treated with 3,5-dimethyl-N-nitro-1H-pyrazole-1-carboximidamide in methanol to give a nitroguanidine derivative, from which the nitro group was removed by catalytic transfer hydrogenation. The methodology is exemplified by the development of efficient preparative routes to agmatine and hirudonine. The integrity of the sequence of protection/deprotection leading to hirudonine was confirmed by a crystal-structure analysis of its sulfate. The effect of selected compounds on the uptake of putrescine into rat lung cells was determined and showed that N 4-(4-azidobenzyloxycarbonyl)spermidine was the best inhibitor (Ki = 3.4 µM).

  本文描述了制备多胺衍生物1,4-二氨基丁烷（腐胺）和N-（3-氨基丙基）-1,4-二氨基丁烷（精胺）的方法，其中特定的氨基被修饰为胍基等官能团。在这些多胺中，特定的氨基被保护成N-三氟乙酰基和N-4-叠氮苄氧羰基衍生物，并分别使用甲醇氨和二硫苏糖醇-三乙胺选择性地脱去保护。通过改进的方法引入胍基官能团，其中氨基与3,5-二甲基-N-硝基-1H-吡唑-1-羧酰亚胺在甲醇中反应生成硝基胍衍生物，然后通过催化转移氢化除去硝基。该方法以开发高效的制备路线至胍氨酸和蛭素为例。保护/去保护序列的完整性通过其硫酸盐的晶体结构分析得到了证实。评估了选定化合物对大鼠肺细胞摄取腐胺的影响，并显示N-4-（4-叠氮苄氧羰基）精胺是最好的抑制剂（Ki = 3.4 µM）。
• Discrimination of spermidine amino functions by a new protecting group strategy; application to the synthesis of guanidinylated polyamines, including hirudonine
  作者：Andrew Mitchinson、Bernard T. Golding、Roger J. Griffin、Mary C. O'Sullivan

  DOI：10.1039/c39940002613

  日期：——

  Agmatine and hirudonine, guanidine derivatives of putrescine and spermidine, respectively, are synthesised by the application of a new protecting group strategy for polyamines, which uses N-nitroguanidinyl as a precursor of guanidine functions and selectively blocks spermidine at N-1 and N-8 with trifluoroacetyl and at N-4 by 4-azidobenzyloxycarbonyl.

  从尸胺和亚精胺分别合成的阿基美汀和水蛭素是通过采用一种新的聚胺保护基团策略实现的，该策略使用N-硝基氨基脲作为氨基功能的前体，并选择性地在N-1和N-8位用三氟乙酰基保护亚精胺，而在N-4位用4-叠氮苯甲氧羰基进行保护。
• A stereorational total synthesis of (−)-ptilocaulin
  作者：Alan E. Walts、William R. Roush

  DOI：10.1016/s0040-4020(01)96701-8

  日期：1985.1

  A stereorational total synthesis of the structurally (−)-enantiomer of the unique guanidine containing natural product ptilocaulin is described. This efficient synthesis (14 steps, 7.4% overall yield) utilizes an intramolecular 1,3-dipolar cycloaddition as a key step and establishes that the natural product is the most stable of a number of possible isomers. This work also establishes the absolute

  描述了独特的含有胍的天然产物枯草杆菌蛋白酶的结构（-）-对映异构体的立体全合成。这种高效的合成方法（14个步骤，总收率7.4％）利用分子内1,3-偶极环加成作为关键步骤，并确定了天然产物是多种可能异构体中最稳定的。这项工作还建立了枯草杆菌蛋白酶的绝对立体化学，如式3所示。