2-甲基-3-正丙基吡咯 | 75145-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-甲基-3-正丙基吡咯
• 英文名称: 2-Methyl-3-n-propylpyrrole
• 英文别名: 2-methyl-3-propyl-1H-pyrrole
• CAS: 75145-97-0
• 化学式: C₈H₁₃N
• mdl: MFCD02823179
• 分子量: 123.198
• InChiKey: XXIMYGNNKLURQG-UHFFFAOYSA-N

物化性质

• 沸点：
  71-72 °C(Press: 5 Torr)
• 密度：
  0.9071 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-甲基-3-正丙基吡咯 、 4-甲氧基-2,2'-联吡咯-5-甲醛 在 PigC from Pseudomonas putida pig-r2 ΔpigD strain 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 4″-propylprodigiosin
  参考文献：
  名称：

  New Prodigiosin Derivatives Obtained by Mutasynthesis in Pseudomonas putida

  摘要：

  The deeply red-colored natural compound prodigiosin is a representative of the prodiginine alkaloid family, which possesses bioactivities as antimicrobial, antitumor, and antimalarial agents. Various bacteria including the opportunistic human pathogen Serratia marcescens and different members of the Streptomycetaceae and Pseudoalteromonadaceae produce prodiginines. In addition, these microbes generally accumulate many structurally related alkaloids making efficient prodiginine synthesis and purification difficult and expensive. Furthermore, it is known that structurally different natural prodiginine variants display differential bioactivities. In the herein described mutasynthesis approach, 13 different derivatives of prodigiosin were obtained utilizing the GRAS (generally recognized as safe) classified strain Pseudomonas putida KT2440. Genetic engineering of the prodigiosin pathway together with incorporation of synthetic intermediates thus resulted in the formation of a so far unprecedented structural diversity of new prodiginine derivatives in P. putida. Furthermore, the formed products allow reliable conclusions regarding the substrate specificity of PigC, the final condensing enzyme in the prodigiosin biosynthesis pathway of S. marcescens. The biological activity of prodigiosin toward modulation of autophagy was preserved in prodiginine derivatives. One prodiginine derivative displayed more potent autophagy inhibitory activity than the parent compound or the synthetic clinical candidate obatoclax.

  DOI：

  10.1021/acssynbio.7b00099
• 作为产物：
  描述：

  2-己酮 在 盐酸羟胺 、 sodium acetate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 2-甲基-3-正丙基吡咯
  参考文献：
  名称：

  新的灵菌红衍生物——化学酶合成和针对顺铂耐药癌细胞的生理学评价

  摘要：

  灵菌红及其来自灵菌素家族的衍生物是一类天然的细菌来源的次生代谢生物碱。众所周知，它们对多种细菌、病原真菌、寄生虫和几种癌细胞系具有多种生物活性。天然衍生物的生物合成基于联吡咯前体 MBC 和各种取代的单吡咯之间最终 ATP 和酶依赖性缩合反应的聚合路线。尽管这些连接酶已被认为与单吡咯有关的混杂性，但仍进行了少量研究来调查 MBC 衍生物的混杂性。为了克服目前结构知识的缺乏，我们合成了六个 5′- nMBC 的 β-烷基衍生物，并通过连接酶 PigC、TreaP 和 TamQ 验证其与单吡咯缩合的适用性，以通过实验探测其活性位点。此外，对 A 环上具有5- n-烷基化的化学合成的 prodiginines 进行了系统的细胞活力筛选，其中包括尿路上皮癌细胞系 RT-112（顺铂敏感）和 RT-112 res（顺铂耐药），以了解供电子取代基对细胞毒性的影响。除了 PigC、TreaP 和 TamQ

  DOI：

  10.1039/d3cy00913k

文献信息

• Pyrroles from ketoximes and acetylene. 29. Synthesis of alkylpyrroles from dialkylketoximes and dichloroethane by reaction with KOH-DMSO
  作者：B. A. Trofimov、A. I. Mikhaleva、A. N. Vasil'ev、S. E. Korostova、S. G. Shevchenko

  DOI：10.1007/bf00505898

  日期：1985.1
• TROFIMOV, B. A.;MIXALEVA, A. I.;VASILEV, A. N.;KOROSTOVA, S. E.;SHEVCHENK+, XIMIYA GETEROTSIKL. SOEDIN., 1985, N 1, 59-62
  作者：TROFIMOV, B. A.、MIXALEVA, A. I.、VASILEV, A. N.、KOROSTOVA, S. E.、SHEVCHENK+

  DOI：——

  日期：——
• New Prodigiosin Derivatives Obtained by Mutasynthesis in <i>Pseudomonas putida</i>
  作者：Andreas S. Klein、Andreas Domröse、Patrick Bongen、Hannah U. C. Brass、Thomas Classen、Anita Loeschcke、Thomas Drepper、Luca Laraia、Sonja Sievers、Karl-Erich Jaeger、Jörg Pietruszka

  DOI：10.1021/acssynbio.7b00099

  日期：2017.9.15

  The deeply red-colored natural compound prodigiosin is a representative of the prodiginine alkaloid family, which possesses bioactivities as antimicrobial, antitumor, and antimalarial agents. Various bacteria including the opportunistic human pathogen Serratia marcescens and different members of the Streptomycetaceae and Pseudoalteromonadaceae produce prodiginines. In addition, these microbes generally accumulate many structurally related alkaloids making efficient prodiginine synthesis and purification difficult and expensive. Furthermore, it is known that structurally different natural prodiginine variants display differential bioactivities. In the herein described mutasynthesis approach, 13 different derivatives of prodigiosin were obtained utilizing the GRAS (generally recognized as safe) classified strain Pseudomonas putida KT2440. Genetic engineering of the prodigiosin pathway together with incorporation of synthetic intermediates thus resulted in the formation of a so far unprecedented structural diversity of new prodiginine derivatives in P. putida. Furthermore, the formed products allow reliable conclusions regarding the substrate specificity of PigC, the final condensing enzyme in the prodigiosin biosynthesis pathway of S. marcescens. The biological activity of prodigiosin toward modulation of autophagy was preserved in prodiginine derivatives. One prodiginine derivative displayed more potent autophagy inhibitory activity than the parent compound or the synthetic clinical candidate obatoclax.
• New prodigiosin derivatives – chemoenzymatic synthesis and physiological evaluation against cisplatin-resistant cancer cells
  作者：Tim Moritz Weber、Alexandra Leyens、Lena Berning、Björn Stork、Jörg Pietruszka

  DOI：10.1039/d3cy00913k

  日期：——

  (cisplatin-sensitive) and RT-112res (cisplatin-resistant) to fathom the effect of electron-donating substituents on cytotoxicity. Alongside an overall broad acceptance of short- and medium-chain alkylated MBC derivatives by the enzymes PigC, TreaP, and TamQ, we identified the A-ring substituted prodiginines with methyl substituents as superior anticancer agents against cisplatin-resistant RT-112res after 72 h (15.7–18

  灵菌红及其来自灵菌素家族的衍生物是一类天然的细菌来源的次生代谢生物碱。众所周知，它们对多种细菌、病原真菌、寄生虫和几种癌细胞系具有多种生物活性。天然衍生物的生物合成基于联吡咯前体 MBC 和各种取代的单吡咯之间最终 ATP 和酶依赖性缩合反应的聚合路线。尽管这些连接酶已被认为与单吡咯有关的混杂性，但仍进行了少量研究来调查 MBC 衍生物的混杂性。为了克服目前结构知识的缺乏，我们合成了六个 5′- nMBC 的 β-烷基衍生物，并通过连接酶 PigC、TreaP 和 TamQ 验证其与单吡咯缩合的适用性，以通过实验探测其活性位点。此外，对 A 环上具有5- n-烷基化的化学合成的 prodiginines 进行了系统的细胞活力筛选，其中包括尿路上皮癌细胞系 RT-112（顺铂敏感）和 RT-112 res（顺铂耐药），以了解供电子取代基对细胞毒性的影响。除了 PigC、TreaP 和 TamQ