3-吡唑烷酮,5-甲基- | 10234-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 3-吡唑烷酮,5-甲基-
• 英文名称: 5-methyl-pyrazolidin-3-one
• 英文别名: (RS)-5-methylpyrazolidin-3-one；5-methylpyrazolidin-3-one；5-Methyl-pyrazolidin-3-on；5-methyl-3-pyrazolidinone
• CAS: 10234-76-1
• 化学式: C₄H₈N₂O
• mdl: MFCD08444486
• 分子量: 100.12
• InChiKey: WYVJDRGXWOXCCH-UHFFFAOYSA-N

物化性质

• 沸点：
  147 °C(Press: 4 Torr)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-吡唑烷酮,5-甲基- 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 3-氨基丁酰胺
  参考文献：
  名称：

  Stetter,H.; Findeisen,K., Chemische Berichte, 1965, vol. 98, p. 3228 - 3235

  摘要：

  DOI：
• 作为产物：
  描述：

  巴豆酸 在 aluminum oxide 一水合肼 作用下， 以 正丁醇 、 苯 为溶剂， 以69%的产率得到3-吡唑烷酮,5-甲基-
  参考文献：
  名称：

  Tandem photochemical synthesis of N-amino .beta.-lactams from pyrazolidin-3-ones

  摘要：

  DOI：

  10.1021/jo00311a023

文献信息

• Isatin <i>N</i>,<i>N</i>′-Cyclic Azomethine Imine 1,3-Dipole and Abnormal [3 + 2]-Cycloaddition with Maleimide in the Presence of 1,4-Diazabicyclo[2.2.2]octane
  作者：Xiao Wang、Peng Yang、Yong Zhang、Chao-Zhe Tang、Fang Tian、Lin Peng、Li-Xin Wang

  DOI：10.1021/acs.orglett.6b03815

  日期：2017.2.3

  A new isatin N,N′-cyclic azomethine imine synthon was devised, and an unexpected abnormal [3 + 2]-cycloaddition with maleimide catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) has been disclosed. A variety of tricyclic spiropyrrolidine oxindoles bearing a dinitrogen heterocycle and succinimide scaffold were obtained in excellent yields (up to 96%) and diastereoselectivities (up to 97:3) under mild

  设计了一种新的Isatin N，N'-环甲亚胺亚胺合子，并公开了1,4-二氮杂双环[2.2.2]辛烷（DABCO）催化的马来酰亚胺意外异常[3 + 2]-环加成反应。在温和条件下，以优异的收率（高达96％）和非对映选择性（高达97：3）获得了多种带有二氮杂环和琥珀酰亚胺支架的三环螺吡咯烷恶唑。
• [EN] ARYLMETHYLIDENE HETEROCYCLES AS NOVEL ANALGESICS<br/>[FR] HÉTÉROCYCLES D'ARYLMÉTHYLIDÈNE COMME NOUVEAUX ANALGÉSIQUES
  申请人：CHLORION PHARMA INC

  公开号：WO2009097695A1

  公开（公告）日：2009-08-13

  The present invention relates to Arylmethylidene heterocycles, compositions comprising an Arylmethylidene heterocycle, and methods useful for treating or preventing pain comprising administering an effective amount of an Arylmethylidene heterocycle as depicted by the formula (Ia).The compounds, compositions, and methods of the invention are also useful for treating or preventing inflammation.

  本发明涉及芳基甲基亚甲基杂环化合物，包括含有芳基甲基亚甲基杂环化合物的组合物，以及用于治疗或预防疼痛的方法，包括给予如公式(Ia)所示的芳基甲基亚甲基杂环化合物的有效量。该发明的化合物、组合物和方法也适用于治疗或预防炎症。
• Discovery of a Flexible Triazolylbutanoic Acid as a Highly Potent Uric Acid Transporter 1 (URAT1) Inhibitor
  作者：He Tian、Wei Liu、Zhixing Zhou、Qian Shang、Yuqiang Liu、Yafei Xie、Changying Liu、Weiren Xu、Lida Tang、Jianwu Wang、Guilong Zhao

  DOI：10.3390/molecules21111543

  日期：——

  In order to systematically explore and understand the structure–activity relationship (SAR) of a lesinurad-based hit (1c) derived from the replacement of the S atom in lesinurad with CH2, 18 compounds (1a–1r) were designed, synthesized and subjected to in vitro URAT1 inhibitory assay. The SAR exploration led to the discovery of a highly potent flexible URAT1 inhibitor, 1q, which was 31-fold more potent than parent lesinurad (IC50 = 0.23 μM against human URAT1 for 1q vs 7.18 μM for lesinurad). The present study discovered a flexible molecular scaffold, as represented by 1q, which might serve as a promising prototype scaffold for further development of potent URAT1 inhibitors, and also demonstrated that the S atom in lesinurad was not indispensable for its URAT1 inhibitory activity.

  为了系统地探索和理解基于lesinurad的命中化合物（1c）的结构-活性关系（SAR），该化合物是通过将lesinurad中的S原子替换为CH2得到的，设计并合成了18个化合物（1a–1r），并对其进行了体外URAT1抑制活性测试。SAR探索发现了一个高效的柔性URAT1抑制剂1q，其活性比母体lesinurad高31倍（对于人URAT1的IC50值，1q为0.23 μM，而lesinurad为7.18 μM）。本研究发现了一种柔性分子骨架，如1q所示，这可能作为进一步开发高效URAT1抑制剂的有前景的原型骨架，并且表明lesinurad中的S原子对其URAT1抑制活性并非必需。
• Structural effects in pyrazolidinone-mediated organocatalytic Diels–Alder reactions
  作者：Eoin Gould、Tomas Lebl、Alexandra M.Z. Slawin、Mark Reid、Andrew D. Smith

  DOI：10.1016/j.tet.2010.09.021

  日期：2010.11

  promoted Diels–Alder reactions evaluated. Systematic variation of the C(5)- and N(2)-substituents indicates that the incorporation of an electron withdrawing substitutent at N(2) and either a Ph or CF3 substitution at C(5) results in optimal catalytic activity. The diastereoisomeric resolution of a model C(5)-Ph substituted pyrazolidinone and its ability to impart modest levels of asymmetric induction

  制备了一系列吡唑烷丁-3-酮，并评估了它们作为亚胺离子促进的Diels-Alder反应的催化剂的活性。C（5）-和N（2）-取代基的系统变化表明，在N（2）引入吸电子取代基和在C（5）取代Ph或CF 3导致最佳的催化活性。还证明了模型C（5）-Ph取代的吡唑烷酮的非对映异构体拆分及其在有机催化Diels-Alder反应中赋予适度水平的不对称诱导的能力。
• Tetrahydro-1H,5H-pyrazolo[1,2-a]pyrazole-1-carboxylates as inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase
  作者：Nika Strašek、Lara Lavrenčič、Andraž Oštrek、Dejan Slapšak、Uroš Grošelj、Marina Klemenčič、Helena Brodnik Žugelj、Jernej Wagger、Marko Novinec、Jurij Svete

  DOI：10.1016/j.bioorg.2019.102982

  日期：2019.8

  The reactions between 5-substituted pyrazolidine-3-ones, aldehydes, and methyl methacrylate provided tetrahydropyrazolo[1,2-a]pyrazole-1-carboxylates as mixtures of syn- and anti-diastereomers. Testing for inhibition of dihydroorotate dehydrogenase of Plasmodium falciparum (PfDHODH) revealed high activity of some anti-isomers of the methyl esters, while the corresponding carboxylic acids and carboxamides

  5-取代的吡唑烷-3-酮，醛和甲基丙烯酸甲酯之间的反应提供了四氢吡唑并[1,2-a]吡唑-1-羧酸酯，为顺式和反式非对映异构体的混合物。测试对恶性疟原虫（PfDHODH）的二氢乳清酸脱氢酶的抑制作用表明，某些甲酯的抗异构体具有很高的活性，而相应的羧酸和羧酰胺则没有活性。活性最高的代表是（1S *，3S *，5R *）-1,5-二甲基-7-氧代-3-苯基四氢-1H，5H-吡唑并[1,2-a]吡唑-1-羧酸酯（IC50 = 2.9±0.3μM），而且对人源酶PfDHODH / HsDHODH> 350也表现出很高的选择性。根据分子对接分数，这种高活性可以通过甲基的协同作用来解释，苯基和CO2Me取代基在酶的活性位点具有疏水口袋。衍生自该化合物的羧酸和羧酰胺不抑制PfDHODH。