isopropyl pyrrole-2-carboxylate | 35889-88-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: isopropyl pyrrole-2-carboxylate
• 英文别名: isopropyl 1H-pyrrole-2-carboxylate；propan-2-yl 1H-pyrrole-2-carboxylate；pyrrole-2-carboxylic acid isopropyl ester
• CAS: 35889-88-4
• 化学式: C₈H₁₁NO₂
• mdl: MFCD20542535
• 分子量: 153.181
• InChiKey: YFUQSHFYYFRUCE-UHFFFAOYSA-N

物化性质

• 沸点：
  251.8±13.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  isopropyl pyrrole-2-carboxylate 在 lithium 作用下， 以 四氢呋喃 、 氨 为溶剂， 生成 1-O-tert-butyl 5-O-propan-2-yl 5-[hydroxy(phenyl)methyl]-2H-pyrrole-1,5-dicarboxylate
  参考文献：
  名称：

  Reductive aldol reactions on aromatic heterocycles

  摘要：

  The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductive aldol reaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction of pyrroles could be oxidised and then reduced with NaBH4 to provide syn-aldol adducts with high levels of stereoselectivity. The relative stereochemistry of two adducts was proven by X-ray crystallography. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02224-8
• 作为产物：
  描述：

  吡咯-2-羧酸 在 草酰氯 作用下， 生成 isopropyl pyrrole-2-carboxylate
  参考文献：
  名称：

  Reductive aldol reactions on aromatic heterocycles

  摘要：

  The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductive aldol reaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction of pyrroles could be oxidised and then reduced with NaBH4 to provide syn-aldol adducts with high levels of stereoselectivity. The relative stereochemistry of two adducts was proven by X-ray crystallography. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02224-8

文献信息

• Reduction of electron-deficient pyrroles using group I and II metals in ammonia
  作者：Timothy J. Donohoe、Paul M. Guyo、Roy L. Beddoes、Madeleine Helliwell

  DOI：10.1039/a707661d

  日期：——

  The preparation and Birch reduction of a series of electron-deficient pyrroles is described. This methodology allows the synthesis of a variety of C-2 substituted 3-pyrrolines‡ in good to excellent yields. The role of various activating groups (amide, ester, carbamate and urea) has been examined with regard to both stability under the Birch conditions and ease of deprotection after reduction. In addition, we discovered that the 3-pyrroline skeleton can be oxidised at C-5 with chromium trioxide–3,5-dimethylpyrazole to form the 3-pyrrolin-2-one nucleus. The identity of the Birch reduced products and also of the oxidised 3-pyrrolin-2-ones has been confirmed by X-ray crystallography on two derivatives.

  描述了一系列缺电子吡咯的制备和伯奇还原。这种方法允许以良至优秀的产率合成各种C-2取代的3-吡咯啉。研究了不同的活化基团（酰胺、酯、氨基甲酸酯和脲）在伯奇反应条件下的稳定性以及还原后去保护的难易程度。此外，我们发现3-吡咯啉骨架可以用三氧化铬和3,5-二甲基吡唑在C-5位氧化，形成3-吡咯啉-2-酮核。通过对两个衍生物的X射线晶体学确定了伯奇还原产物以及氧化的3-吡咯啉-2-酮的身份。
• [EN] HETEROCYCLIC COMPOUNDS AND MEDICAL USE THEREOF<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEUR UTILISATION MÉDICALE
  申请人：FOND TELETHON

  公开号：WO2020104558A1

  公开（公告）日：2020-05-28

  The present invention relates to heterocyclic nitrogen compounds, use thereof as a medicament and pharmaceutical compositions thereof. Furthermore, the invention provides combinations of compounds of general formula (I) with therapeutic agents, such as correctors, potentiators and amplifiers of dysfunctional proteins.

  本发明涉及杂环氮化合物，其用作药物和药物组成物。此外，本发明提供了通式(I)化合物与治疗剂的组合，如修正剂、增强剂和功能异常蛋白质的增强剂。
• 2-Sulfonyl-4-chloroanilino Moiety:  A Potent Pharmacophore for the Anti-Human Immunodeficiency Virus Type 1 Activity of Pyrrolyl Aryl Sulfones
  作者：Marino Artico、Romano Silvestri、Silvio Massa、Anna G. Loi、Simona Corrias、Giovanna Piras、Paolo La Colla

  DOI：10.1021/jm950568w

  日期：1996.1.1

  The synthesis and the evaluation of cytotoxicity and anti-HIV-1 activity of new aryl pyrrolyl (8) and aryl indolyl (9) sulfones are reported. Preparation of above sulfones was achieved by reacting arylsulfonyl chlorides with substituted pyrroles and indoles or by condensing sulfonamides with 2,5-dimethoxytetrahydrofuran in glacial acetic acid according to the Clauson-Kaas method. Chemical requisites

  据报道合成了新的芳基吡咯基（8）和芳基吲哚基（9）砜，并对其细胞毒性和抗HIV-1活性进行了合成和评估。根据Clauson-Kaas方法，通过使芳基磺酰氯与取代的吡咯和吲哚反应，或通过将磺酰胺与2，5-二甲氧基四氢呋喃在冰醋酸中缩合，来制备上述砜。与这些化合物的抗HIV-1活性有关的化学要求是2-磺酰基-4-氯苯胺基部分和吡咯环2位的烷氧羰基。用乙氧基羰基和异丙氧基羰基取代基获得最佳的活性和选择性。药效基团部分的氨基取代导致无活性的产物（烷基化）或减弱的（酰化）抗HIV-1活性。在测试衍生物中，16种化合物的EC50值在10至1 microM之间，五种（8b'，d'，f'，h'j'）的EC50S在亚微摩尔范围内。这些化合物对野生型和AZT耐药菌株的HIV-1有活性，但对HIV-2没有活性。此外，在酶分析中，它们有效抑制了HIV-1重组逆转录酶，对耐奈韦拉平和TIBO耐药菌株的酶活性降低了1
• Ryanoids and related compounds — Chemoselective electrocatalytic hydrogenation of alkyl α-pyrrole carboxylates: Selective hydrogenation of ryanodine
  作者：Luc Ruest、Hugues Ménard、Vincent Moreau、François Laplante

  DOI：10.1139/v02-182

  日期：2002.12.1

  A study of the electrocatalytic hydrogenation (ECH) process of pyrrole and different alkyl pyrrole-2-carboxylates is presented. Once hydrogenated, the alkyl pyrrole-2-carboxylate becomes an ester of proline, an important natural amino acid. The process is chemoselective to the pyrrole ring. Ryanodine is a natural ryanoid known to be biologically active. The tetrahydroryanodine derivative thus obtained

  介绍了吡咯和不同烷基吡咯-2-羧酸盐的电催化加氢 (ECH) 过程的研究。一旦氢化，吡咯-2-羧酸烷基酯变成脯氨酸的酯，脯氨酸是一种重要的天然氨基酸。该过程对吡咯环具有化学选择性。Ryanodine 是一种已知具有生物活性的天然 ryanoid。如此获得的四氢兰尼定衍生物现在可以代表具有高度生物学意义的分子。兰尼碱的氢化可以通过电催化和催化过程进行。在这两种情况下，反应都不是非对映选择性的。关键词：电催化加氢，脯氨酸酯，兰尼丁，四氢兰尼丁。
• Insight on pyrimido[5,4-g]indolizine and pyrimido[4,5-c]pyrrolo[1,2-a]azepine systems as promising photosensitizers on malignant cells
  作者：Marilia Barreca、Angela Maria Ingarra、Maria Valeria Raimondi、Virginia Spanò、Michele De Franco、Luca Menilli、Valentina Gandin、Giorgia Miolo、Paola Barraja、Alessandra Montalbano

  DOI：10.1016/j.ejmech.2022.114399

  日期：2022.7

  Searching for new small molecules as photosensitizing agents, we have developed a class of twenty-five pyrimido[5,4-g]indolizine and pyrimido[4,5-c]pyrrolo[1,2-a]azepines with a good substitution pattern defining a versatile synthetic pathway to approach the title ring system. All compounds were evaluated for their photocytotoxicity on a triple negative human breast cancer cell line (MDA-MB-231) in

  寻找新的小分子作为光敏剂，我们开发了一类具有良好取代模式的 25 种嘧啶并[5,4- g ]中氮茚和嘧啶并[4,5 - c ]吡咯并[1,2- a ]氮杂定义了一种通用的合成途径来接近标题环系统。在黑暗和 UVA 光 (2.0 J/cm 2 )下评估所有化合物对三阴性人乳腺癌细胞系 (MDA-MB-231) 的光细胞毒性。最有效的化合物具有光抗增殖活性，IC 50值高达纳摩尔范围。有趣的是，这些新开发的化合物相对于非癌性细胞显示出对癌细胞的高选择性。此外，四种代表性衍生物也被证明对另一种人 HER2 阳性乳腺癌细胞系 (HCC1954) 和具有 Hras 突变的 HER2 阳性膀胱癌细胞系 (T24) 具有光毒性。在三阴性 MDA-MB-231 癌细胞中进行的机制研究揭示了这些化合物增加活性氧 (ROS) 产生和诱导硫醇氧化还原应激的能力，从而通过细胞凋亡触发癌细胞死亡。在高度侵袭性和转移性