6-amino-4-(2-bromophenyl)-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile | 625368-87-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-amino-4-(2-bromophenyl)-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• 英文别名: 3-Methyl-6-amino-4-(2-bromophenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
• CAS: 625368-87-8
• 化学式: C₁₄H₁₁BrN₄O
• 分子量: 331.172
• InChiKey: QLFYNNXVNUZXMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.72
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-amino-4-(2-bromophenyl)-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile 、 水杨醛 、 zinc(II) chloride 反应 72.17h， 生成 Zn[2‐bromophenylsalicylaldiminemethylpyranopyrazole]Cl₂
  参考文献：
  名称：

  作为新型纳米结构席夫碱配合物和用于合成吡喃并[2,3-d]嘧啶二酮衍生物的催化剂的纳米锌[2-硼氧苯基水杨醛亚胺基甲基吡喃并吡唑] Cl2

  摘要：

  制备了一种新型的纳米结构的席夫碱复合物纳米Zn [2-硼苯基苯基水杨醛亚胺基甲基吡喃并吡唑] Cl 2（nano [Zn-2BSMP] Cl 2），并使用多种技术对其进行了表征。纳米[Zn-2BSMP] Cl 2被用作通过丙二腈，芳基醛和巴比妥酸衍生物的多组分反应制备某些吡喃并[2,3- d ]嘧啶二酮衍生物的有效催化剂。与其他报道的催化剂相比，纳米[Zn-2BSMP] Cl 2作为催化剂的新颖性和效率是这项工作的主要特征。

  DOI：

  10.1002/aoc.4584
• 作为产物：
  描述：

  3-甲基-3-吡唑啉-5-酮 、 2-[(2-溴苯基)亚甲基]丙二腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以77%的产率得到6-amino-4-(2-bromophenyl)-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  Dihydropyrano [2,3-c] pyrazole: Novel in vitro inhibitors of yeast α-glucosidase

  摘要：

  Inhibition of alpha-glucosidase enzyme activity is a reliable approach towards controlling post-prandial hyperglycemia associated risk factors. During the current study, a series of dihydropyrano[ 2,3-c] pyrazoles (1-35) were synthesized and evaluated for their a-glucosidase inhibitory activity. Compounds 1, 4, 22, 30, and 33 were found to be the potent inhibitors of the yeast alpha-glucosidase enzyme. Mechanistic studies on most potent compounds reveled that 1, 4, and 30 were non-competitive inhibitors (K-i = 9.75 +/- 0.07, 46 +/- 0.0001, and 69.16 +/- 0.01 mu M, respectively), compound 22 is a competitive inhibitor (K-i = 190 +/- 0.016 mu M), while 33 was an uncompetitive inhibitor (K-i = 45 +/- 0.0014 mu M) of the enzyme. Finally, the cytotoxicity of potent compounds (i.e. compounds 1, 4, 22, 30, and 33) was also evaluated against mouse fibroblast 3T3 cell line assay, and no toxicity was observed. This study identifies non-cytotoxic novel inhibitors of alpha-glucosidase enzyme for further investigation as anti-diabetic agents. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2016.01.008

文献信息

• Bovine serum albumin: An efficient and green biocatalyst for the one-pot four-component synthesis of pyrano[2,3-c]pyrazoles
  作者：Xingtian Huang、Zhipeng Li、Dongyang Wang、Yiqun Li

  DOI：10.1016/s1872-2067(15)61088-9

  日期：2016.9

  four-component reaction of aryl aldehydes, malononitrile, hydrazine hydrate, and ethyl acetoacetate for the synthesis of pyrano[2,3-c]pyrazoles under mild reaction conditions. The BSA biocatalyst also displayed a high catalytic affinity for acyclic/cyclic ketones to yield the corresponding pyrano[2,3-c]pyrazoles or their spirocyclic variants. The BSA could be used for at least five cycles without serious loss

  生物催化剂的使用在化学催化领域引起了越来越多的关注。在这里，我们已经证明，牛血清白蛋白 (BSA) 是一种普遍存在的、廉价的、非酶促转运蛋白，可以在芳基醛、丙二腈、水合肼、和乙酰乙酸乙酯用于在温和的反应条件下合成吡喃并[2,3-c]吡唑。BSA 生物催化剂还显示出对无环/环状酮的高催化亲和力，以产生相应的吡并 [2,3-c] 吡唑或其螺环变体。BSA 可以使用至少五个循环而不会严重损失催化活性。这种新颖、高效的协议具有产量高、操作简单和相对温和的环境影响等优点。而且，
• Synthesis of Substituted Pyranopyrazoles under Neat Conditions via a Multicomponent Reaction
  作者：Boreddy Reddy、Arasampattu Nagarajan

  DOI：10.1055/s-0029-1217526

  日期：2009.7

  A simple and efficient synthesis of pyranopyrazoles in good yields via a four-component reaction between an aromatic aldehyde, hydrazine hydrate, ethyl acetoacetate and malononitrile under neat conditions is described.

  描述了一种简单高效的吡喃并吡唑合成方法：在无溶剂条件下，通过芳香醛、水合肼、乙酰乙酸乙酯与丙二腈的四组分反应，以良好的产率得到目标产物。
• Synthesis of pyranopyrazoles using isonicotinic acid as a dual and biological organocatalyst
  作者：Mohammad Ali Zolfigol、Mahsa Tavasoli、Ahmad Reza Moosavi-Zare、Parvin Moosavi、Hendrik Gerhardus Kruger、Morteza Shiri、Vahid Khakyzadeh

  DOI：10.1039/c3ra45289a

  日期：——

  In this study, a green, simple and efficient method for the preparation of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles by means of a one-pot four component condensation reaction of aryl aldehydes, ethyl acetoacetate, malononitrile and hydrazine hydrate is reported. The reaction utilizes isonicotinic acid as a dual and biological organocatalyst at 85 °C under solvent-free conditions.

  在这项研究中，报道了一种绿色、简单且高效的方法，通过采用苯基醛、乙酰乙酸乙酯、马隆腈和水合肼的一锅四组分缩合反应制备6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-二氢吡喃[2,3-c]吡唑。这一反应在无溶剂条件下，以85 °C的温度下，采用异烟酸作为双重生物有机催化剂。
• Highly functionalized pyranopyrazoles: synthesis, antimicrobial activity, simulation studies and their structure activity relationships (SARs)
  作者：Guda Mallikarjuna Reddy、Gundala Sravya、Gutha Yuvaraja、Alexandre Camilo、Grigory V. Zyryanov、Jarem Raul Garcia

  DOI：10.1007/s11164-018-3569-8

  日期：2018.12

  the present work synthesis, simulation, and antimicrobial studies of pyranopyrazole derivatives were discussed. Among the reported compounds, 4b has dominant antimicrobial activity that was due to its higher dipole moment. Also, this compound has the most hydrophilic nature and low E g value. Besides, compound 4e has the next higher dipole moment, hydrophilic property and efficient biological activity

  摘要 有效的抗菌和抗真菌剂的开发是治疗领域中一项永恒而又不懈的研究。尽管如此，医学研究仍希望找到最好的抗菌剂。为了达到这个目的，在这里，讨论了吡喃并吡唑衍生物的当前工作合成，模拟和抗菌研究。在报告的化合物中，由于其较高的偶极矩， 4b 具有显着的抗菌活性。而且，该化合物具有最亲水的性质和较低的 E g值。此外，化合物 4e 具有更高的偶极矩，亲水性和有效的生物活性。这些结果的基本原理说明，将电子结果与生物学数据进行比较是找到有效药物化合物的更好方法。 图形概要
• Synthesis of Pyranopyrazoles under Eco-friendly Approach by Using Acid Catalysis
  作者：Guda Mallikarjuna Reddy、Jarem Raul Garcia

  DOI：10.1002/jhet.2544

  日期：2017.1

  Multicomponent synthesis of pyranopyrazole derivatives by using montmorillonite K‐10 as a reusable green acid catalyst under eco‐friendly method in the presence of eco‐friendly solvent leads to novel protocol. Moreover, catalyst could be reused five times for the reaction without noticeable loss of activity. The scope of this path was to develop new synthetic molecules by using green catalysis for further

  在环境友好型溶剂存在下，以环境友好型方法，将蒙脱土K-10用作可重复使用的绿色酸催化剂，可进行多组分合成吡喃并吡唑衍生物，从而产生了新颖的方案。而且，催化剂可重复使用五次以进行反应而没有明显的活性损失。该途径的范围是通过使用绿色催化进行进一步的筛选，例如用于有机电子材料和生物测定的起始分子，来开发新的合成分子。