1-异丙基-1H-吡咯-2-甲醛 | 23373-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-异丙基-1H-吡咯-2-甲醛
• 英文名称: 1-prop-2-yl-2-pyrrolecarboxaldehyde
• 英文别名: 1-i-Propyl-2-formylpyrrol；1-isopropyl-1H-pyrrole-2-carbaldehyde；1-isopropyl-pyrrole-2-carbaldehyde；1-propan-2-ylpyrrole-2-carbaldehyde
• CAS: 23373-77-5
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: UOQYIUGOKYHBSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-异丙基-1H-吡咯-2-甲醛 在 氢氧化钾 、 四丁基氟化铵 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 0.5h， 生成 (E)-3-(1-Isopropyl-5-pyridin-3-ylmethyl-1H-pyrrol-2-yl)-2-methyl-acrylic acid
  参考文献：
  名称：

  [(1H-Imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl]pyrroles as thromboxane synthetase inhibitors

  摘要：

  Several [(1H-imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl] pyrroles were prepared and evaluated in vitro as thromboxane synthetase inhibitors in human platelet aggregation studies. A number of structures, e.g. 10b,f,g,i (respective IC50 values: 1 microM, 50 nM, 42 nM, 44 nM) showed superior in vitro inhibition of TXA2 synthetase when compared to the standard dazoxiben (1). However, it was found that in vitro potency did not translate into nor correlate with in vivo activity when these compounds were evaluated in mice in a collagen-epinephrine-induced pulmonary thromboembolism model. (E)-1-Methyl-2-[(1H-imidazol-1-yl)methyl]-5-(2-carboxyprop-1-enyl) pyrrole (10b) was found to offer protection against collagen-epinephrine-induced mortality in mice, thereby demonstrating that oral administration is an effective route for absorption of this drug. Additional evidence for the oral effectiveness of 10b in lowering serum TXB2 levels was obtained by performing ex vivo radioimmunoassay experiments with rats. A 13-week study of 10b in rats with reduced renal mass was conducted in order to evaluate the role of TXA2 production in hypertension and renal dysfunction. Although serum and urinary TXB2 levels in rats were found to be lowered during this study by 10b, the levels of urinary protein excretion remained comparable to that of the control group.

  DOI：

  10.1021/jm00124a027
• 作为产物：
  描述：

  N-isopropylpyrrole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 生成 1-异丙基-1H-吡咯-2-甲醛
  参考文献：
  名称：

  [(1H-Imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl]pyrroles as thromboxane synthetase inhibitors

  摘要：

  Several [(1H-imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl] pyrroles were prepared and evaluated in vitro as thromboxane synthetase inhibitors in human platelet aggregation studies. A number of structures, e.g. 10b,f,g,i (respective IC50 values: 1 microM, 50 nM, 42 nM, 44 nM) showed superior in vitro inhibition of TXA2 synthetase when compared to the standard dazoxiben (1). However, it was found that in vitro potency did not translate into nor correlate with in vivo activity when these compounds were evaluated in mice in a collagen-epinephrine-induced pulmonary thromboembolism model. (E)-1-Methyl-2-[(1H-imidazol-1-yl)methyl]-5-(2-carboxyprop-1-enyl) pyrrole (10b) was found to offer protection against collagen-epinephrine-induced mortality in mice, thereby demonstrating that oral administration is an effective route for absorption of this drug. Additional evidence for the oral effectiveness of 10b in lowering serum TXB2 levels was obtained by performing ex vivo radioimmunoassay experiments with rats. A 13-week study of 10b in rats with reduced renal mass was conducted in order to evaluate the role of TXA2 production in hypertension and renal dysfunction. Although serum and urinary TXB2 levels in rats were found to be lowered during this study by 10b, the levels of urinary protein excretion remained comparable to that of the control group.

  DOI：

  10.1021/jm00124a027

文献信息

• Direct and Efficient Synthesis of Pyrrole-3-carbaldehydes by Vilsmeier-Haack Formylation of Pyrroles with Sterically Crowded Amides
  作者：Mikhail Kuznetsov、Petr Ilyin、Alena Pankova

  DOI：10.1055/s-0031-1290763

  日期：2012.5

  Abstract A simple and convenient synthetic method to prepare N-substituted pyrrole-3-carbaldehydes by Vilsmeier–Haack formylation of pyrroles using sterically crowded formamides was developed. The dependence of the formylation regioselectivity on steric features of substrates and reagents is discussed. A simple and convenient synthetic method to prepare N-substituted pyrrole-3-carbaldehydes by Vilsmeier–Haack

  摘要 开发了一种简单方便的合成方法，该方法通过使用空间拥挤的甲酰胺，通过Vilsmeier-Haack对吡咯进行甲酰化来制备N-取代的吡咯3-甲醛。讨论了甲酰化区域选择性对底物和试剂空间特征的依赖性。 开发了一种简单方便的合成方法，该方法通过使用空间拥挤的甲酰胺，通过Vilsmeier-Haack对吡咯进行甲酰化来制备N-取代的吡咯3-甲醛。讨论了甲酰化区域选择性对底物和试剂空间特征的依赖性。
• One-Pot Amberlyst 15-Controlled Cyclocondensation of Piperidines and Arylaldehydes: Synthesis of 3,5-Diarylmethylpyridines
  作者：Meng-Yang Chang、Yu-Lin Tsai

  DOI：10.1021/acs.joc.9b03315

  日期：2020.4.17

  Amberlyst 15-controlled one-pot easy-operational intermolecular cyclocondensation of substituted piperidines with arylaldehydes provides diversified 3,5-diarylmethylpyridines in high to excellent yields under refluxing toluene conditions. The uses of various acidic solid supports and reaction solvents are investigated for facile and efficient transformation. A plausible mechanism has been proposed

  在芳基醛回流下，Amberlyst 15受控的一锅式易操作的哌啶与芳醛的分子间环缩合反应提供了多样化的3,5-二芳基甲基吡啶。研究了各种酸性固体载体和反应溶剂的使用，以实现简便高效的转化。已经提出了一种合理的机制。
• Novel 4,5-Bis (4-methoxyphenyl)-2-(pyrrol-2-yl) thiazoles and
  申请人：Kanebo, Ltd.

  公开号：US04659726A1

  公开（公告）日：1987-04-21

  Novel 4,5-bis(4-methoxyphenyl)-2-(pyrrol-2-yl)-thiazoles of the formula: ##STR1## wherein R.sup.1 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, 2,2,2-trifluoroethyl, a group of the formula: --CH.sub.2 COOR.sup.2 R.sup.2 is C.sub.1-8 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, or phenyl-C.sub.1-2 alkyl), or a group of the formula: --(CH.sub.2).sub.n --A--R.sup.3 (A is oxygen or sulfur, R.sup.3 is C.sub.1-4 alkyl or C.sub.2-4 alkenyl, and n is 1, 2 or 3), a process for the preparation of the compounds, and a pharmaceutical composition useful as a platelet aggregation inhibitor which comprises as an active ingredient the above 4,5-bis(4-methoxyphenyl)-2-(pyrrol-2-yl)thiazole compound in admixture with a conventional pharmaceutically acceptable carrier or diluent.

  化合物的结构式为：##STR1## 其中R1为C1-4烷基，C2-4烯基，C2-4炔基，2,2,2-三氟乙基，一个公式为：--CH2COOR2的基团R2为C1-8烷基，C2-4烯基，C2-4炔基或苯基-C1-2烷基），或一个公式为：--（CH2）n-A-R3（其中A为氧或硫，R3为C1-4烷基或C2-4烯基，n为1、2或3），制备该化合物的方法，以及一种制剂，其作为血小板聚集抑制剂有用，所述制剂包括上述4,5-双（4-甲氧基苯基）-2-（吡咯-2-基）噻唑化合物与传统药学可接受的载体或稀释剂的混合物作为活性成分。
• Jasmonate derivatives and compositions thereof
  申请人：Nanocare Technologies, Inc.

  公开号：US10314918B2

  公开（公告）日：2019-06-11

  The disclosure describes jasmonate conjugates and nanocarried and/or microcarried jasmonate conjugates and pharmaceutical compositions thereof, as well as use thereof for treating or preventing angiogenesis-related or NF-κB-related disorders. Also disclosed are methods of making the conjugates.

  本公开描述了茉莉酸盐共轭物、纳米载体和/或微载体茉莉酸盐共轭物及其药物组合物，以及其在治疗或预防血管生成相关疾病或 NF-κB 相关疾病方面的用途。还公开了制造这些共轭物的方法。
• Novel 4,5-bis(4-methoxyphenyl)-2-(pyrrol-2-yl)thiazoles, process for the preparation thereof and pharmaceutical composition containing the same
  申请人：KANEBO, LTD.

  公开号：EP0159677B1

  公开（公告）日：1989-02-22