2-(2,5-二甲基-1H-吡咯-1-基)-5-碘吡啶 | 477889-91-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-(2,5-二甲基-1H-吡咯-1-基)-5-碘吡啶
• 英文名称: 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-iodopyridine
• 英文别名: 2-(2,5-dimethylpyrrol-1-yl)-5-iodopyridine
• CAS: 477889-91-1
• 化学式: C₁₁H₁₁IN₂
• 分子量: 298.126
• InChiKey: XPDQEPPMUTUFGT-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  359.8±42.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(2,5-二甲基-1H-吡咯-1-基)-5-碘吡啶 在 盐酸 、 盐酸羟胺 、 三乙胺 、 copper(l) chloride 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 2-氯-5-甲氧基吡啶
  参考文献：
  名称：

  通过改良的 Negishi 交叉偶联反应合成不同双取代的 2,2'-联吡啶

  摘要：

  已经开发了通过应用改良的 Negishi 交叉偶联条件从取代的 2-溴-和 2-氯吡啶中获得许多不同二取代的 2,2'-联吡啶的通用实用方法。这些 2,2'-联吡啶带有多功能的官能团，可以进一步细化，如一些例子所示。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300192
• 作为产物：
  描述：

  2-氨基-5-碘吡啶 、 2,5-己二酮 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以81%的产率得到2-(2,5-二甲基-1H-吡咯-1-基)-5-碘吡啶
  参考文献：
  名称：

  使用三氟乙酸钾通过流动系统实现芳香族和杂芳香族化合物的快速有效的三氟甲基化

  摘要：

  追根溯源：芳基/杂芳基碘化物的三氟甲基化已被证明使用流动系统，从而实现快速反应。使用 CF 3 CO 2 K 作为三氟甲基源，以良好到极好的收率制备了广谱的三氟甲基化化合物。该方法具有反应时间短的优点并使用方便的[CF 3 ]源。

  DOI：

  10.1002/anie.201306094

文献信息

• Enantio‐ and Regioselective NiH‐Catalyzed Reductive Hydroarylation of Vinylarenes with Aryl Iodides
  作者：Yuli He、Chuang Liu、Lei Yu、Shaolin Zhu

  DOI：10.1002/anie.202010386

  日期：2020.11.23

  A highly enantio‐ and regioselective hydroarylation process of vinylarenes with aryl halides has been developed using a NiH catalyst and a new chiral bis imidazoline ligand. A broad range of structurally diverse, enantioenriched 1,1‐diarylalkanes, a structure found in a number of biologically active molecules, have been obtained with excellent yields and enantioselectivities under extremely mild conditions

  使用NiH催化剂和新型手性双咪唑啉配体开发了乙烯基芳烃与芳基卤化物的高度对映和区域选择性加氢芳基化方法。在极其温和的条件下，以优异的收率和对映选择性获得了多种结构多样的，对映体富集的1,1-二芳基烷烃，该结构存在于许多生物活性分子中。
• Pyridine and pyrimidine analogs of acetaminophen as inhibitors of lipid peroxidation and cyclooxygenase and lipoxygenase catalysis
  作者：Tae-gyu Nam、Susheel J. Nara、Irène Zagol-Ikapitte、Thomas Cooper、Luca Valgimigli、John A. Oates、Ned A. Porter、Olivier Boutaud、Derek A. Pratt

  DOI：10.1039/b912528k

  日期：——

  Herein we report an investigation of the efficacy of pyridine and pyrimidine analogs of acetaminophen (ApAP) as peroxyl radical-trapping antioxidants and inhibitors of enzyme-catalyzed lipid peroxidation by cyclooxygenases (COX) and lipoxygenases (LOX). In inhibited autoxidations we find that ApAP, the common analgesic and antipyretic agent, is a very good antioxidant with a rate constant for reaction with peroxyl radicals (kinh = 5 × 105 M−1 s−1) that is higher than many widely-used phenolic antioxidants, such as the ubiquitous butylated hydroxytoluene (BHT). This reactivity is reduced substantially upon incorporation of nitrogen into the phenolic ring, owing to an increase in the O–H bond dissociation enthalpy of pyridinols and pyrimidinols with respect to phenols. Incorporation of nitrogen into the phenolic ring of ApAP was also found to decrease its efficacy as an inhibitor of prostaglandin biosynthesis by ovine COX-1 (oCOX-1). This is explained on the basis of an increase in its oxidation potential and its reduced reactivity as a reducing co-substrate of the peroxidase protoporphyrin. In contrast, the efficacy of ApAP as an inhibitor of lipid hydroperoxide biosynthesis by soybean LOX-1 (sLOX-1) increased upon incorporation of nitrogen into the ring, suggesting a different mechanism of inhibition dependent on the acidity of the phenolic O–H which may involve chelation of the catalytic non-heme iron atom. The greater stability of the 3-pyridinols and 5-pyrimidinols to air oxidation as compared to phenols allowed us to evaluate some electron-rich pyridinols and pyrimidinols as inhibitors of oCOX-1 and sLOX-1. While the pyridinols had the best combination of activities as antioxidants and inhibitors of oCOX-1 and sLOX-1, they were found to be more toxic than ApAP in preliminary assays in human hepatocellular carcinoma (HepG2) cell culture. The pyrimidinols, however, were up to 17-fold more reactive to peroxyl radicals and up to 25-fold better inhibitors of prostaglandin biosynthesis than ApAP, with similar cytotoxicities to HepG2 cells at high levels of exposure.

  在此，我们报告了对吡啶和嘧啶类对乙酰氨基酚（ApAP）作为过氧自由基捕获抗氧化剂以及环氧合酶（COX）和脂氧合酶（LOX）催化的脂质过氧化反应抑制剂的有效性研究。在抑制的自氧化反应中，我们发现，作为常用的镇痛和退烧药物的ApAP，是一种非常好的抗氧化剂，其与过氧自由基的反应速率常数（kinh = 5 × 10^5 M−1 s−1）高于许多广泛使用的酚类抗氧化剂，如普遍存在的丁基羟基甲苯（BHT）。由于吡啶醇和嘧啶醇的O–H键解离焓相比于酚类有所增加，导致将氮引入酚环后，其反应性大幅降低。ApAP酚环中氮的引入也发现减少了其作为羔羊COX-1（oCOX-1）前列腺素生物合成抑制剂的有效性。这可以通过其氧化电位的增加以及其作为过氧化氢酶原卟啉还原共底物的反应性降低来解释。相较之下，ApAP作为大豆LOX-1（sLOX-1）对脂质过氧化氢生物合成的抑制剂的有效性在引入氮元素后有所提高，这表明其抑制机制可能依赖于酚类O–H的酸度，可能涉及对催化性非血红素铁原子的螯合。相比于酚类，3-吡啶醇和5-嘧啶醇对空气氧化的稳定性更高，使我们能够评估一些富电子的吡啶醇和嘧啶醇作为oCOX-1和sLOX-1的抑制剂。尽管吡啶醇在抗氧化剂和oCOX-1、sLOX-1抑制剂的活性方面表现最佳，但在对人类肝细胞癌（HepG2）细胞培养的初步实验中发现其毒性明显高于ApAP。然而，嘧啶醇对过氧自由基的反应性高达ApAP的17倍，对前列腺素生物合成的抑制效果好达ApAP的25倍，在高浓度暴露下，其对HepG2细胞的细胞毒性相似。
• HIV inhibiting 3,4-dihydro-imidazo[4,5-B]pyridin-5-ones
  申请人：Tibotec Pharmaceuticals Ltd.

  公开号：US07994187B2

  公开（公告）日：2011-08-09

  HIV inhibitory compounds of formula: salts, hydrates, solvates, N-oxides, or stereoisomers thereof, wherein A forms pyridine, pyrimidine, pyrazine, pyridazine, triazine, imidazole, pyrazole, triazole, tetrazole, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, and thiadiazole; R1 is halo, cyano, nitro, C1-6alkyl, polyhaloC1-6alkyl, —C1-6alkyl-OR4, —C(═O)—R5, —C(═O)—OR4, —C(═O)—NR6R7, —OR4, —O—C(═O)—C1-6alkyl, —O—C1-6alkyl-OR4, —O—C1-6alkyl-NR6R7, —O—C1-6alkyl-O—C(═O)—C1-6alkyl, —O—C1-6alkyl-C(═O)—OR4, —O—C1-6alkyl-C(═O)—NR6R7, —NR6R7, —NR8—C(═O)—R5, —NR8—C(═O)—OR4, —NR8—C(═O)—NR6R7, —NR8—C(═O)—C1-6alkyl-C(═O)—OR4, —NR8—C1-6alkyl-OR4, —NR8—C1-6alkyl-NR6R7, —NR8—C1-6alkyl-imidazolyl, —NR8—SO2R9, —N═CH—NR6R7, —NH—C(═NH)—NH2, —SO2NR6R7, and —O—PO(OR8)2; D forms pyridine, pyrimidine, pyrazine, pyridazine, pyrrole, imidazole, pyrazole, furane, oxazole, isoxazole, thiophene, thiazole, and isothiazole; R2 is C1-6alkyl, polyhaloC1-6alkyl, halo, cyano, —COOR4, —OR4, and —NR6R7; R3 is phenyl, pyridyl, pyrimidinyl, imidazopyridyl, pyrazolopyridyl, triazolopyridyl, quinoline, imidazopyrimidinyl, pyrazolopyrimidinyl, triazolopyrimidinyl, pyridopyrimidinyl; which may optionally be substituted; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; pharmaceutical compositions containing these compounds, methods for preparing these compounds and compositions.

  公式为：其中A形成吡啶，嘧啶，吡嗪，吡嗪啉，三嗪，咪唑，吡唑，三唑，四唑，噁唑，异噁唑，氧化噻唑，噻唑，异噻唑和硫代噻唑的盐，水合物，溶剂化合物，N-氧化物或其立体异构体；R1为卤素，氰基，硝基，C1-6烷基，多卤C1-6烷基，-C1-6烷基-OR4，-C（═O）-R5，-C（═O）-OR4，-C（═O）-NR6R7，-OR4，-O-C（═O）-C1-6烷基，-O-C1-6烷基-OR4，-O-C1-6烷基-NR6R7，-O-C1-6烷基-O-C（═O）-C1-6烷基，-O-C1-6烷基-C（═O）-OR4，-O-C1-6烷基-C（═O）-NR6R7，-NR6R7，-NR8-C（═O）-R5，-NR8-C（═O）-OR4，-NR8-C（═O）-NR6R7，-NR8-C（═O）-C1-6烷基-C（═O）-OR4，-NR8-C1-6烷基-OR4，-NR8-C1-6烷基-NR6R7，-NR8-C1-6烷基-咪唑基，-NR8-SO2R9，-N═CH-NR6R7，-NH-C（═NH）-NH2，-SO2NR6R7和-O-PO（OR8）2；D形成吡啶，嘧啶，吡嗪，吡嗪啉，吡咯，咪唑，吡唑，呋喃，噁唑，异噁唑，噻吩，噻唑和异噻唑；R2为C1-6烷基，多卤C1-6烷基，卤素，氰基，-COOR4，-OR4和-NR6R7；R3为苯基，吡啶基，嘧啶基，咪唑吡啶基，吡唑吡啶基，三唑吡啶基，喹啉，咪唑嘧啶基，吡唑嘧啶基，三唑嘧啶基，吡啶嘧啶基；可以选择地被取代；m为0、1、2或3；n为0、1、2或3；含有这些化合物的制药组合物，制备这些化合物和组合物的方法。
• HIV INHIBITING 3,4-DIHYDRO-IMIDAZO[4,5-B]PYRIDIN-5-ONES
  申请人：Kesteleyn Bart Rudolf Romanie

  公开号：US20090170855A1

  公开（公告）日：2009-07-02

  HIV inhibitory compounds of formula: salts, hydrates, solvates, N-oxides, or stereoisomers thereof, wherein A forms pyridine, pyrimidine, pyrazine, pyridazine, triazine, imidazole, pyrazole, triazole, tetrazole, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, and thiadiazole; R 1 is halo, cyano, nitro, C 1-6 alkyl, polyhaloC 1-6 alkyl, —C 1-6 alkyl-OR 4 , —C(═O)—R 5 , —C(═O)—OR 4 , —C(═O)—NR 6 R 7 , —OR 4 , —O—C(═O)—C 1-6 alkyl, —O—C 1-6 alkyl-OR 4 , —O—C 1-6 alkyl-NR 6 R 7 , —O—C 1-6 alkyl-O—C(═O)—C 1-6 alkyl, —O—C 1-6 alkyl-C(═O)—OR 4 , —O—C 1-6 alkyl-C(═O)—NR 6 R 7 , —NR 6 R 7 , —NR 8 —C(═O)—R 5 , —NR 8 —C(═O)—OR 4 , —NR 8 —C(═O)—NR 6 R 7 , —NR 8 —C(═O)—C 1-6 alkyl-C(═O)—OR 4 , —NR 8 —C 1-6 alkyl-OR 4 , —NR 8 —C 1-6 alkyl-NR 6 R 7 , —NR 8 —C 1-6 alkyl-imidazolyl, —NR 8 —SO 2 R 9 , —N═CH—NR 6 R 7 , —NH—C(═NH)—NH 2 , —SO 2 NR 6 R 7 , and —O—PO(OR 8 ) 2 ; D forms pyridine, pyrimidine, pyrazine, pyridazine, pyrrole, imidazole, pyrazole, furane, oxazole, isoxazole, thiophene, thiazole, and isothiazole; R 2 is C 1 -C 6 alkyl, polyhaloC 1 -C 6 alkyl, halo, cyano, —COOR 4 , —OR 4 , and —NR 6 R 7 ; R 3 is phenyl, pyridyl, pyrimidinyl, imidazopyridyl, pyrazolopyridyl, triazolopyridyl, quinoline, imidazopyrimidinyl, pyrazolopyrimidinyl, triazolopyrimidinyl, pyridopyrimidinyl; which may optionally be substituted; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; pharmaceutical compositions containing these compounds, methods for preparing these compounds and compositions.

  公式为：其中A为吡啶、嘧啶、吡嗪、吡嗪二氮杂环、三嗪、咪唑、吡唑、三唑、四唑、噁唑、异噁唑、噻唑、异噻唑和硫代噻唑；R1为卤素、氰基、硝基、C1-6烷基、多卤C1-6烷基、—C1-6烷基-OR4、—C(═O)—R5、—C(═O)—OR4、—C(═O)—NR6R7、—OR4、—O—C(═O)—C1-6烷基、—O—C1-6烷基-OR4、—O—C1-6烷基-NR6R7、—O—C1-6烷基-O—C(═O)—C1-6烷基、—O—C1-6烷基-C(═O)—OR4、—O—C1-6烷基-C(═O)—NR6R7、—NR6R7、—NR8—C(═O)—R5、—NR8—C(═O)—OR4、—NR8—C(═O)—NR6R7、—NR8—C(═O)—C1-6烷基-C(═O)—OR4、—NR8—C1-6烷基-OR4、—NR8—C1-6烷基-NR6R7、—NR8—C1-6烷基-咪唑基、—NR8—SO2R9、—N═CH—NR6R7、—NH—C(═NH)—NH2、—SO2NR6R7和—O—PO(OR8)2；D为吡啶、嘧啶、吡嗪、吡嗪二氮杂环、吡咯、咪唑、吡唑、呋喃、噁唑、异噁唑、噻吩、噻唑和异噻唑；R2为C1-C6烷基、多卤C1-C6烷基、卤素、氰基、—COOR4、—OR4和—NR6R7；R3为苯基、吡啶基、嘧啶基、咪唑吡啶基、吡唑吡啶基、三唑吡啶基、喹啉、咪唑嘧啶基、吡唑嘧啶基、三唑嘧啶基、吡啶嘧啶基；这些基团可以选择性地被取代；m为0、1、2或3；n为0、1、2或3；含有这些化合物的药物组合物，制备这些化合物和组合物的方法。
• WO2007/113290
  申请人：——

  公开号：——

  公开（公告）日：——