5-氨基-1-苄基吡唑-4-甲酸乙酯 | 19867-62-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1-苄基吡唑-4-甲酸乙酯
• 中文别名: 5-氨基-1-苄基-1H-吡唑-4-羧酸乙酯
• 英文名称: ethyl 5-amino-1-benzyl-1H-pyrazole-4-carboxylate
• 英文别名: 5-amino-1-benzyl-1H-pyrazole-4-carboxylic acid ethyl ester；ethyl 5-amino-1-benzylpyrazole-4-carboxylate
• CAS: 19867-62-0
• 化学式: C₁₃H₁₅N₃O₂
• mdl: MFCD00502757
• 分子量: 245.281
• InChiKey: SDKPSMKNXBQGQU-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C
• 沸点：
  424.9±35.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933199090
• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  5-氨基-1-苄基吡唑-4-甲酸乙酯 在 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 18.0h， 生成 1-benzyl-5-(benzylideneamino)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
  参考文献：
  名称：

  Synthesis of imine-pyrazolopyrimidinones and their mechanistic interventions on anticancer activity

  摘要：

  Design, synthesis and anticancer activity of a series of imine-pyrazolopyrimidinones is reported for the first time. Compounds 9d, 9n and 9o in the series show encouraging in vitro anticancer activity with low micromolar IC50 values against prostate (PC3) and breast (MCF7) cancer cell lines. Some notions about structure-activity relationships and plausible mechanism of biological activity are presented. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.016
• 作为产物：
  描述：

  苄基肼 、 2-氰基-3-乙氧基丙烯酸乙酯 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 5-氨基-1-苄基吡唑-4-甲酸乙酯
  参考文献：
  名称：

  Discovery and Optimization of 5-Amino-1,2,3-triazole-4-carboxamide Series against Trypanosoma cruzi

  摘要：

  Chagas' disease, caused by the protozoan parasite Trypanosoma cruzi, is the most common cause of cardiac-related deaths in endemic regions of Latin America. There is an urgent need for new safer treatments because current standard therapeutic options, benznidazole and nifurtimox, have significant side effects and are only effective in the acute phase of the infection with limited efficacy in the chronic phase. Phenotypic high content screening against the intracellular parasite in infected VERO cells was used to identify a novel hit series of 5-amino-1,2,3-triazole-4-carboxamides (ATC). Optimization of the ATC series gave improvements in potency, aqueous solubility, and metabolic stability, which combined to give significant improvements in oral exposure. Mitigation of a potential Ames and hERG liability ultimately led to two promising compounds, one of which demonstrated significant suppression of parasite burden in a mouse model of Chagas' disease.

  DOI：

  10.1021/acs.jmedchem.7b00463

文献信息

• Chemoenzymatic Asymmetric Total Synthesis of Phosphodiesterase Inhibitors:  Preparation of a Polycyclic Pyrazolo[3,4-<i>d</i>]pyrimidine from an Acylnitroso Diels−Alder Cycloadduct-Derived Aminocyclopentenol
  作者：May Xiao-Wu Jiang、Namal C. Warshakoon、Marvin J. Miller

  DOI：10.1021/jo0484070

  日期：2005.4.1

  Enzymatic resolution of Boc-protected 4-aminocyclopenten-1-ol 4c gave both enantiomers 5c and 6c in high ee. Boc removal and separate condensation with chloropyrazolopyrimidine 18 provided elaborated 1,4-aminocyclopentenol derivatives 20 and 26, respectively. Separate treatment of 20 and 26 with Pd(0) under basic conditions induced cyclization to unsaturated polycycles 22 and 27, which, upon catalytic

  Boc保护的4-氨基环戊烯-1-醇4c的酶解得到了高ee值的对映体5c和6c。Boc的去除和与氯吡唑并嘧啶18的单独缩合分别提供了详细的1，4-氨基环戊烯醇衍生物20和26。在碱性条件下用Pd（0）分别处理20和26诱导环化为不饱和多环22和27，在催化氢化后将其转化为新的含环戊烷的吡唑并嘧啶24和28，是最近描述的新型磷酸二酯酶抑制剂的类似物。
• benzamide derivatives as oxytocin agonists and vasopressin antagonists
  申请人：Ferring B.V.

  公开号：EP1449844A1

  公开（公告）日：2004-08-25

  Novel compounds according to general formula 1, wherein G1 is NR5R6 or a fused polycyclic group that are specific OT receptor agonists and/or Via receptor antagonists. Pharmaceutical compositions comprising such compounds are useful in the treatment of, inter alia, primary dysmenorrhoea.

  根据一般公式1，新化合物中G1为NR5R6或特定的OT受体激动剂和/或Via受体拮抗剂的融合多环基团。包含这类化合物的药物组合物在治疗原发性痛经等方面是有用的。
• Synthesis of some pyrazolo[4,3-<i>e</i>][1,2]- and thiazolo[4,5-<i>e</i>][1,2]thiazine 1,1-dioxide derivatives
  作者：Robert Bellemin、Didier Festal

  DOI：10.1002/jhet.5570210418

  日期：1984.7

  The synthesis of various 2-methylpyrazolo[4,3-e]- and thiazolo[4,5-e][1,2]thiazine 1,1-dioxide derivatives is described.

  描述了各种2-甲基吡唑并[4，3- e ]-和噻唑并[4，5- e ] [1,2]噻嗪1，1-二氧化物衍生物的合成。
• Facile synthesis of 1-substituted 4,5-diaminopyrazoles and its application toward the synthesis of pyrazolo[3,4- b ]pyrazines
  作者：Tun-Cheng Chien、Ronald A. Smaldone、Leroy B. Townsend

  DOI：10.1016/j.tetlet.2004.03.142

  日期：2004.5

  5-aminopyrazole-4-carboxylates. The acyl azides undergo a Curtius rearrangement followed by quenching with alcohols to form the corresponding carbamates. The 1-substituted 5-amino-4-benzyloxycarbonylaminopyrazoles were unblocked by catalytic hydrogenolysis to give the desired 4,5-diaminopyrazoles. These 4,5-diaminopyrazoles were immediately condensed with glyoxal to afford 1-substituted pyrazolo[3,4-b]pyrazines.

  由适当的5-氨基吡唑-4-羧酸酯制备1-取代的5-氨基吡唑-4-羰基叠氮化物。酰基叠氮化物经历Curtius重排，然后用醇淬灭以形成相应的氨基甲酸酯。通过催化氢解解封1-取代的5-氨基-4-苄氧基羰基氨基吡唑，得到所需的4，5-二氨基吡唑。立即将这些4，5-二氨基吡唑与乙二醛缩合，得到1-取代的吡唑并[3，4- b ]吡嗪。
• Oxytocin agonists
  申请人：——

  公开号：US20040235753A1

  公开（公告）日：2004-11-25

  Compounds according to general formula 1, wherein G 1 is NR 6 R 7 or a group according to general formula 3 and G 2 NR 24 R 25 or a fused polycyclic group are novel. They are selective and potent oxytocin agonists. Pharmaceutical compositions of such compounds are useful in the treatment of, inter alia, erectile dysfunction. 1

  公式1中的化合物，其中G1是NR6R7或根据公式3的基团，G2是NR24R25或融合的多环基团，是新颖的选择性和有效的催产素激动剂。这些化合物的药物组成物在治疗勃起功能障碍等方面是有用的。