5,7-二甲基吡唑并嘧啶-2-羧酸 | 587-54-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 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: 5,7-二甲基吡唑并嘧啶-2-羧酸
• 中文别名: 3-(苯甲酰基氨基)苯甲酸
• 英文名称: 3-benzamidobenzoic acid
• 英文别名: 3-(Benzoylamino)benzoic acid
• CAS: 587-54-2
• 化学式: C₁₄H₁₁NO₃
• mdl: MFCD00157843
• 分子量: 241.246
• InChiKey: WXTOAZQBWHSIQN-UHFFFAOYSA-N

物化性质

• 熔点：
  252.5°C
• 沸点：
  384.01°C (rough estimate)
• 密度：
  1.5100

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  5,7-二甲基吡唑并嘧啶-2-羧酸 在 ruthenium trichloride 吡啶 、 氢氧化钾 、 sodium periodate 、 氯化亚砜 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 25.0h， 生成 N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylsulfonyl)phneyl 3-[(N'-benzoyl-N'-methyl)amino]benzamide
  参考文献：
  名称：

  WO2006/137395

  摘要：

  公开号：
• 作为产物：
  描述：

  3-benzoylamino-benzoic acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 5,7-二甲基吡唑并嘧啶-2-羧酸
  参考文献：
  名称：

  Structure-Based Design and Synthesis of Novel Inhibitors Targeting HDAC8 from Schistosoma mansoni for the Treatment of Schistosomiasis

  摘要：

  Schistosomiasis is a major neglected parasitic disease that affects more than 265 million people worldwide and for which the control strategy consists of mass treatment with the only available drug, praziquantel. In this study, a series of new benzohydroxamates were prepared as potent inhibitors of Schistosoma mansoni histone deacetylase 8 (smHDAC8). Crystallographic analysis provided insights into the: inhibition mode of smHDAC8 activity by these 3-amidobenzohydroxamates. The newly designed inhibitors were evaluated in screens for enzyme inhibitory activity against schistosome and human HDACs. Twenty-seven compounds were found to be active in the nanomolar range, and some of them showed selectivity toward smHDAC8 over the major human HDACs (I and 6). The active benzohydroxamates were additionally screened for lethality against the schistosome larval stage using a fluorescence-based assay. Four of these showed significant dose-dependent killing of the schistosome larvae and markedly impaired egg laying of adult worm pairs maintained in culture.

  DOI：

  10.1021/acs.jmedchem.5b01478

文献信息

• Acylated 1<i>H</i>-1,2,4-Triazol-5-amines Targeting Human Coagulation Factor XIIa and Thrombin: Conventional and Microscale Synthesis, Anticoagulant Properties, and Mechanism of Action
  作者：Marvin Korff、Lukas Imberg、Jonas M. Will、Nico Bückreiß、Svetlana A. Kalinina、Benjamin M. Wenzel、Gregor A. Kastner、Constantin G. Daniliuc、Maximilian Barth、Ruzanna A. Ovsepyan、Kirill R. Butov、Hans-Ulrich Humpf、Matthias Lehr、Mikhail A. Panteleev、Antti Poso、Uwe Karst、Torsten Steinmetzer、Gerd Bendas、Dmitrii V. Kalinin

  DOI：10.1021/acs.jmedchem.0c01635

  日期：2020.11.12

  We herein report the conventional and microscale parallel synthesis of selective inhibitors of human blood coagulation factor XIIa and thrombin exhibiting a 1,2,4-triazol-5-amine scaffold. Structural variations of this scaffold allowed identifying derivative 21i, a potent 29 nM inhibitor of FXIIa, with improved selectivity over other tested serine proteases and also finding compound 21m with 27 nM

  我们在此报告了常规和微观并行合成的人类凝血因子XIIa和凝血酶的选择性抑制剂，这些抑制剂表现出1,2,4-三唑-5-胺骨架。该支架的结构变异允许鉴定衍生物21i（一种有效的FXIIa抑制剂29nM），具有比其他经过测试的丝氨酸蛋白酶更高的选择性，还可以发现化合物21m对凝血酶具有27 nM的抑制活性。首次证明酰化的1,2,4-三唑-5-胺具有抗凝特性，并具有影响凝血酶和癌细胞诱导的血小板凝集的能力。进行的质谱分析和分子建模使我们能够发现合成的抑制剂与FXIIa活性位点之间以前未知的相互作用，从而揭示了FXIIa抑制的机理细节。合成的化合物代表了开发新的抗血栓药物或化学工具以研究FXIIa和凝血酶在生理和病理过程中的作用的有希望的起点。
• Brine-Mediated Efficient Benzoylation of Primary Amines and Amino Acids
  作者：Gautam Chattopadhyay、Suchandra Chakraborty、Chandan Saha

  DOI：10.1080/00397910802250929

  日期：2008.11.3

  Abstract Benzoylation of primary amines and amino acids is efficiently carried out in a brine solution using a stoichiometric amount of benzoyl chloride followed by trituration with aqueous saturated bicarbonate solution.

  摘要 伯胺和氨基酸的苯甲酰化在盐水溶液中使用化学计量的苯甲酰氯有效地进行，然后用饱和碳酸氢盐水溶液研磨。
• Design and synthesis of 8-substituted benzamido-phenylxanthine derivatives as MAO-B inhibitors
  作者：Bo Song、Tong Xiao、Xiaolu Qi、Ling-Na Li、Kuiyou Qin、Siyun Nian、Guo-Xin Hu、Yinfei Yu、Guang Liang、Faqing Ye

  DOI：10.1016/j.bmcl.2011.12.094

  日期：2012.2

  Monoamine oxidase-B (MAO-B) inhibitor has been used as neuroprotectants to treat the motor deficits of Parkinson‘s disease (PD). We designed and synthesized a class of 8-substituted benzamido-phenylxanthine derivatives as MAO-B inhibitors. The compounds have various inhibitory effects, with compound 6a having a Ki value of 0.26 μM. Their promising activity in vitro suggests potential use in the treatment

  单胺氧化酶-B（MAO-B）抑制剂已被用作神经保护剂，以治疗帕金森氏病（PD）的运动功能障碍。我们设计并合成了一类8取代的苯甲酰氨基-苯基黄嘌呤衍生物作为MAO-B抑制剂。该化合物具有多种抑制作用，其中化合物6a的K i值为0.26μM。它们在体外的有希望的活性暗示了其在PD治疗中的潜在用途。
• 1H and13C chemical shifts for 2-aryl and 2-N-arylamino benzothiazole derivatives
  作者：S. Billeau、F. Chatel、M. Robin、R. Faure、J.-P. Galy

  DOI：10.1002/mrc.1704

  日期：2006.1

  The 1H and 13C NMR resonances for forty‐three 2‐aryl and 2‐N‐arylamino benzothiazole derivatives were completely assigned using a concerted application of one‐ and two‐dimensional experiments (DEPT, gs‐COSY, gs‐HMQC and gs‐HMBC). Copyright © 2005 John Wiley & Sons, Ltd.

  43 种 2-芳基和 2-N-芳基氨基苯并噻唑衍生物的 1H 和 13C NMR 共振完全使用一维和二维实验（DEPT、gs-COSY、gs-HMQC 和 gs-HMBC ）。版权所有 © 2005 John Wiley & Sons, Ltd.
• COMPOSITION FOR PREVENTING HARMFUL ORGANISMS
  申请人：Kawahara Nobuyuki

  公开号：US20090162453A1

  公开（公告）日：2009-06-25

  There is a harmful organism that cannot be controlled or is difficult to be controlled with the use of a single agent of a compound represented by the general formula (1) according to the invention, an insecticide, a miticide or a fungicide. Accordingly, an object of the invention is to provide a composition for preventing harmful organisms for efficiently controlling such a harmful organism. That is, the invention is directed to a composition for preventing harmful organisms, characterized by comprising the compound represented by the general formula (1) and other insecticides, miticides or fungicides as active ingredients, wherein, in the formula, A 1 , A 2 , A 3 and A 4 independently represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom, G 1 and G 2 independently represent an oxygen atom or a sulfur atom; R 1 and R 2 independently represent a hydrogen atom or a C 1 to C 4 alkyl group; Xs may be the same or different and represent a hydrogen atom, a halogen atom or a trifluoromethyl group; Q 1 represents a substituent such as a phenyl group or a heterocyclic group; and Q 2 represents a substituent such as a phenyl group or a heterocyclic group.)

  这是一个用于有效控制无法用单一化合物代理根据发明所述的一般式（1）所代表的化合物，杀虫剂，杀螨剂或杀菌剂难以控制或难以控制的有害生物的对象。因此，本发明的目的是提供一种用于有效控制此类有害生物的组合物。 换句话说，本发明涉及一种用于预防有害生物的组合物，其特征在于包括一般式（1）所代表的化合物和其他杀虫剂，杀螨剂或杀菌剂作为活性成分， 其中，在该式中，A 1 ，A 2 ，A 3 和A 4 独立地表示碳原子，氮原子或氧化氮原子，G 1 和G 2 独立地表示氧原子或硫原子；R 1 和R 2 独立地表示氢原子或C 1 至C 4 烷基基团；Xs可以相同也可以不同，并表示氢原子，卤原子或三氟甲基基团；Q 1 表示取代基，如苯基或杂环基；Q 2 表示取代基，如苯基或杂环基。