3-cyclopentyl-2-propynoic acid | 6053-88-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-cyclopentyl-2-propynoic acid
• 英文别名: 3-cyclopentylprop-2-ynoic acid；3-cyclopentylpropiolic acid
• CAS: 6053-88-9
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: SFSJZLUMVZEDDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyclopentyl-2-propynoic acid 在 4-二甲氨基吡啶 、 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 N24229-76-A1
  参考文献：
  名称：

  [EN] CHEMICAL COMPOUNDS
  [FR] COMPOSÉS CHIMIQUES

  摘要：

  本发明涉及取代的杂芳基衍生物。具体而言，本发明涉及根据公式Q的化合物：其中D、L、M、W、X、Y和Z在此定义。本发明的化合物是DNA甲基转移酶（DNMT）活性的抑制剂，包括DNMT1、DNMT3a或DNMT3b，并且可用于治疗癌症和过度增殖性疾病。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明还进一步涉及使用本发明的化合物或包含本发明化合物的药物组合物来抑制DNMT活性和治疗相关疾病的方法。

  公开号：

  WO2013062945A1
• 作为产物：
  描述：

  ethyl 3-cyclopentylpropiolate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以197 mg的产率得到3-cyclopentyl-2-propynoic acid
  参考文献：
  名称：

  Structural design and synthesis of arylalkynyl amide-type peroxisome proliferator-activated receptor γ (PPARγ)-selective antagonists based on the helix12-folding inhibition hypothesis

  摘要：

  Peroxisome proliferator-activated receptor gamma (PPAR gamma) antagonists are candidates for treatment of type 2 diabetes, obesity and osteoporosis. However, few rational design strategies are currently available. Here, we utilized the helix12 (H12)-folding inhibition hypothesis, in combination with our previously determined X-ray crystal structure of PPAR gamma agonist MEKT-21 (6) complexed with the PPAR gamma ligand-binding domain, to design and develop a potent phenylalkynyl amide-type PPAR gamma antagonist 9i, focusing initially on pinpoint structural modification of the propanoic acid moiety of 6. Since 9i retained very weak, but distinct, PPAR gamma agonist activity, we next modified the distal benzene ring of 9i, aiming to delete the residual PPAR gamma agonist activity while retaining the antagonist activity. Introduction of a chlorine atom at the 2-position of the distal benzene ring afforded 9p, which exhibited potent, PPAR gamma-selective full antagonist activity without detectable agonist activity. We found that 9p stabilized the corepressor PPAR gamma complex and suppressed basal PPAR gamma activity. This compound showed anti-adipogenesis activity at the cellular level. This agonist antagonist switching concept based on the H12-folding inhibition hypothesis should also be applicable for designing other classes of PPAR gamma full antagonists. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.017

文献信息

• Synthesis of novel imidazole-based triheterocycles via a domino Ugi/Michael reaction and silver-catalyzed heteroannulation
  作者：Zhenghua Li、Yaping Zhao、Guilong Tian、Yi He、Gonghua Song、Luc Van Meervelt、Erik V. Van der Eycken

  DOI：10.1039/c6ra23180b

  日期：——

  An efficient and diversity-oriented synthetic strategy for novel triheterocyclic imidazo-pyrrolo-pyrazine/diazepine/diazocine derivatives is elaborated. The process utilizes a domino four-component Ugi reaction/Michael reaction of imidazole-2-carbaldehyde, propargyl amines, 2-alkynoic acids and isonitriles to deliver functionalized imidazole-pyrrolones, which upon a silver-catalyzed heteroannulation

  阐述了一种有效的，面向多样性的新型三杂环咪唑-吡咯并吡嗪/二氮杂/重氮衍生物的合成策略。该方法利用咪唑-2-甲醛，炔丙基胺，2-炔酸和异腈的多米诺骨牌四组分Ugi反应/迈克尔反应来生成官能化的咪唑-吡咯烷酮，在微波辐射下，银在水性介质中催化异环化，从而制得功能化的咪唑-吡咯烷酮。所需的三杂环化合物具有良好的收率或优异的收率。
• Flash carboxylation: fast lithiation–carboxylation sequence at room temperature in continuous flow
  作者：Bartholomäus Pieber、Toma Glasnov、C. O. Kappe

  DOI：10.1039/c4ra01442a

  日期：——

  A method for the direct lithiation of terminal alkynes and heterocycles with subsequent carboxylation in a continuous flow format was developed. This method provides carboxylic acids at ambient conditions within less than five seconds with only little excess of the organometallic base and CO2.

  开发了一种以连续流形式直接将末端炔烃和杂环锂化并随后进行羧化的方法。该方法在环境条件下在不到五秒的时间内提供了羧酸，而有机金属碱和CO 2几乎没有过量。
• Carbon Dioxide Capture and Use: Organic Synthesis Using Carbon Dioxide from Exhaust Gas
  作者：Seung Hyo Kim、Kwang Hee Kim、Soon Hyeok Hong

  DOI：10.1002/anie.201308341

  日期：2014.1.13

  A carbon capture and use (CCU) strategy was applied to organic synthesis. Carbon dioxide (CO2) captured directly from exhaust gas was used for organic transformations as efficiently as hyper‐pure CO2 gas from a commercial source, even for highly air‐ and moisture‐sensitive reactions. The CO2 capturing aqueous ethanolamine solution could be recycled continuously without any diminished reaction efficiency

  碳捕获和利用（CCU）策略已应用于有机合成。直接从废气中捕获的二氧化碳（CO 2）与来自商业来源的超纯CO 2气体一样有效地用于有机转化，即使是对空气和湿气敏感的反应也是如此。捕获CO 2的乙醇胺水溶液可以连续循环而不会降低反应效率。
• CHEMICAL COMPOUNDS
  申请人：GlaxoSmithKline Intellectual Property (No.2) Limited

  公开号：US20140296204A1

  公开（公告）日：2014-10-02

  The invention is directed to substituted heteroaryl derivatives. Specifically, the invention is directed to compounds according to Formula Q: wherein D, L, M, W, X, Y, and Z are defined herein. The compounds of the invention are inhibitors of DNA methyltransferase (DNMT) activity—including DNMT1, DNMT3a, or DNMT3b—and are useful in the treatment of cancer and hyperproliferative diseases. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting DNMT activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及取代杂环基衍生物。具体而言，本发明涉及符合公式Q的化合物：其中D、L、M、W、X、Y和Z在此定义。本发明的化合物是DNA甲基转移酶（DNMT）活性的抑制剂，包括DNMT1、DNMT3a或DNMT3b，并且在癌症和高增殖性疾病的治疗中有用。因此，本发明进一步涉及包含本发明化合物的制药组合物。本发明还涉及使用本发明化合物或包含本发明化合物的制药组合物抑制DNMT活性和治疗与之相关的疾病的方法。
• Ligand-Free Ag(I)-Catalyzed Carboxylation of Terminal Alkynes with CO₂
  作者：Xiao Zhang、Wen-Zhen Zhang、Xiang Ren、Lin-Lin Zhang、Xiao-Bing Lu

  DOI：10.1021/ol200638z

  日期：2011.5.6

  A convenient approach to selectively prepare a wide range of functionalized propiolic acids was developed by Agl-catalyzed carboxylation of terminal alkynes using carbon dioxide as carboxylative agent under ligand-free conditions.