2-chloromethyl-5-ethyl-pyridine-hydrochloride | 71670-78-5

• 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
• 英文名称: 2-chloromethyl-5-ethyl-pyridine-hydrochloride
• 英文别名: 2-chloromethyl-5-ethyl-pyridine hydrochloride；2-chloromethyl-5-ethylpyridinium chloride；2-(Chloromethyl)-5-ethylpyridine hydrochloride；2-(chloromethyl)-5-ethylpyridine;hydrochloride
• CAS: 71670-78-5
• 化学式: C₈H₁₀ClN*ClH
• 分子量: 192.088
• InChiKey: YWGYPVKLLMLZOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.19
• 重原子数：
  11
• 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：
  14.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloromethyl-5-ethyl-pyridine-hydrochloride 在 manganese triacetate 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 3-ethyl-5-hexyl-7,7-bis(ethoxycarbonyl)-5,6,7,8-tetrahydroquinoline
  参考文献：
  名称：

  Oxidation of diethyl (pyridylmethyl)malonates with manganese(III) acetate, cerium(IV) ammonium nitrate, and iron(III) perchlorate in the presence of alkenes and alkynes

  摘要：

  The oxidation of substituted diethyl 2-, 3-, or 4-picolylmalonates (1a-g) by Mn(III) acetate in acetic acid, Ce(IV) ammonium nitrate in methanol or acetic acid, and Fe(III) perchlorate in acetonitrile in the presence of substituted alkenes (2) and alkynes (3) affords substituted tetra- or dihydroquinolines and/or isoquinolines (4-9) in good to excellent yield. The influence of reaction medium on yield and isomer distribution has been investigated. A mechanism involving oxidative deprotonation of malonic esters by high-valent metal salts to malonyl radicals, their addition to olefins, and intramolecular homolytic substitution to protonated or metal-complexed heteroaromatic bases by the resulting substituted carbon radicals is suggested.

  DOI：

  10.1021/jo00018a024
• 作为产物：
  描述：

  5-乙基-2-甲基-吡啶 在 盐酸 、 氯化亚砜 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 水 为溶剂， 反应 51.0h， 生成 2-chloromethyl-5-ethyl-pyridine-hydrochloride
  参考文献：
  名称：

  5-Lipoxygenase-Activating Protein (FLAP) Inhibitors. Part 4: Development of 3-[3-tert-Butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5-(5-methylpyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethylpropionic Acid (AM803), a Potent, Oral, Once Daily FLAP Inhibitor

  摘要：

  The potent 5-lipoxygenase-activating protein (FLAP) inhibitor 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5-(5-methylpyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethylpropionic acid 11cc is described (AM803, now GSK2190915). Building upon AM103 (1) (Hutchinson et al. J. Med Chem. 2009, 52, 5803-5815; Stock et al. Bioorg. Med. Chem. Lett. 2010, 20, 213-217; Stock et al. Bioorg. Med. Chem. Lett. 2010, 20, 4598-4601), SAR studies centering around the pyridine moiety led to the discovery of compounds that exhibit significantly increased potency in a human whole blood assay measuring LTB4 inhibition with longer drug preincubation times (15 min vs S h). Further studies identified 11cc with a potency of 2.9 nM in FLAP binding, an IC50 of 76 nM for inhibition of LTB4 in human blood (5 h incubation) and excellent preclinical toxicology and pharmacoldnetics in rat and dog. 11cc also demonstrated an extended pharmacodynamic effect in a rodent bronchoalveolar lavage (BAL) model. This compound has successfully completed phase 1 clinical studies in healthy volunteers and is currently undergoing phase 2 trials in asthmatic patients.

  DOI：

  10.1021/jm2008369

文献信息

• Mononuclear iron complexes relevant to nonheme iron oxygenases. Synthesis, characterizations and reactivity of Fe-Oxo and Fe-Peroxo intermediates
  作者：Aurore Thibon、Jean-François Bartoli、Sophie Bourcier、Frédéric Banse

  DOI：10.1039/b913470k

  日期：——

  spectroscopic characteristics of all L(6)(2)4E-Fe complexes are very similar to their TPEN analog. However, [(L(6)(2)4E)FeO](2+) has a greater lifetime than that of [(TPEN)FeO](2+). This can be explained by a restricted bimolecular autodegradation due to the bulkiness provided by the ethyl substituents. Regarding small organic molecule oxidation, [(L(6)(2)4E)FeO](2+) and [(L(6)(2)4E)FeOOH](2+) exhibit behaviours

  新的配体L（6）（2）4E（N，N，N'，N'-四（5-乙基-2-吡啶基甲基）乙烷-1,2-二胺）被设计为TPEN（ N，N，N′，N′-四（2-吡啶基甲基）乙烷-1，2-二胺已被报道具有稳定高价Fe-Oxo和Fe-（氢）过氧的能力。关于后者，L（6）（2）4E中的吡啶基β-取代基不会改变Fe配位化学。使用与TPEN类似物报道的合成方法相同的合成方法，从Fe（II）前体制备[FeO]（2+）和Fe（III）-（氢）过氧中间体。所有L（6）（2）4E-Fe配合物的光谱特征与它们的TPEN类似物非常相似。但是，[（L（6）（2）4E）FeO]（2+）的寿命比[（TPEN）FeO]（2+）的寿命长。这可以解释为由于乙基取代基提供的体积大而导致的双分子自降解受限。关于小有机分子的氧化，[（L（6）（2）4E）FeO]（2+）和[（L（6）（2）4E）FeOOH]（2+）表现出似乎是一般的行为。用T
• Novel thiouracil derivatives pharmaceutical compositions containing them and process for preparing same
  申请人：RICHTER GEDEON VEGYESZETI GYAR RT.

  公开号：EP0391254A3

  公开（公告）日：1991-04-03

  The present invention relates to novel compounds of the general formula (I), wherein R₁ and R₂ stand independently from each other, for hydrogen C₁₋₄alkyl, phenyl, phenyl-C₁₋₄alkyl, piridyl or piridyl-C₁₋₄alkyl group; E means a straight or branched, saturated hydrocarbon chain containing 1 to 6 carbon atoms; R₃ represents: a phenyl group ortho-substituted by a C₂₋₅alkanoylamino, N-C₂₋₅alkanoyl-N-C₁₋₄alkylamino or di(C₁₋₄alkyl)amino group and optionally further substituted by halogen, C₁₋₄alkyl, C₁₋₄alkoxy or C₂₋₅alkanoyloxy group; or a pyridyl group optionally mono- or polysubstituted by halogen, C₁₋₄alkyl, C₁₋₄alkoxy, C₂₋₅alkanoyloxy or phenyl-C₁₋₄alkoxy group as well as their acid addition salts and tautomeric forms of these compounds.The compounds according to the invention show gastric acid secretion-inhibiting and cytoprotective effects and are useful for the treatment of ulcers of the gastrointestinal system.

  本发明涉及一般式（I）的新化合物，其中R₁和R₂分别代表氢、C₁₋₄烷基、苯基、苄基、吡啶基或吡啶基-C₁₋₄烷基；E表示含有1至6个碳原子的直链或支链饱和碳氢链；R₃代表：邻位被C₂₋₅烷酰胺基、N-C₂₋₅烷酰基-N-C₁₋₄烷基胺基或二(C₁₋₄烷基)氨基基取代的苯基，并可选择进一步被卤素、C₁₋₄烷基、C₁₋₄烷氧基或C₂₋₅烷酰氧基取代；或者是吡啶基，可选择被卤素、C₁₋₄烷基、C₁₋₄烷氧基、C₂₋₅烷酰氧基或苯基-C₁₋₄烷氧基单取代或多取代。此外，本发明还涉及这些化合物的酸盐和其异构体形式。根据本发明的化合物显示出抑制胃酸分泌和细胞保护作用，可用于治疗消化系统溃疡。
• Novel thiouracyl derivatives, pharmaceutical compositions containing
  申请人：Richter Gedeon Vegyeszeti Gyar RT

  公开号：US05037830A1

  公开（公告）日：1991-08-06

  The present invention relates to novel compounds of the formula (I), ##STR1## wherein R.sub.1 and R.sub.2 stand independently from each other, for hydrogen, C.sub.1-4 alkyl, phenyl, phenyl-C.sub.1-4 alkyl, piridyl or piridyl-C.sub.1-4 alkyl group; E means a straight or branched, saturated hydrocarbon chain containing 1 to 6 carbon atoms; R.sub.3 represents: a phenyl group ortho-substituted by a C.sub.2-5 alkanoylamino, N-C.sub.2-5 alkanoyl-N-C.sub.1-4 alkylamino or di(C.sub.1-4 alkyl)amino group and optionally further substituted by halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or C.sub.2-5 alkanoyloxy group; or a pyridyl group optionally mono- or polysubstituted by halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.2-5 alkanoyloxy or phenyl-C.sub.1-4 alkoxy group as well as their acid addition salts and tautomeric forms of these compounds. The compounds according to the invention show gastric acid secretion-inhibiting and cytoprotective effects and are useful for the treatment of ulcers of the gastrointestinal system.

  本发明涉及一种新的化合物，其化学式为（I），其中R1和R2分别独立地表示氢、C1-4烷基、苯基、苯基-C1-4烷基、吡啶基或吡啶基-C1-4烷基基团；E表示含1至6个碳原子的直链或支链饱和碳氢链；R3表示：苯基，其邻位取代为C2-5烷酰氨基、N-C2-5烷酰基-N-C1-4烷基氨基或二（C1-4烷基）氨基基团，并且可以进一步取代为卤素、C1-4烷基、C1-4烷氧基或C2-5烷酰氧基；或吡啶基，可以选择单或多取代为卤素、C1-4烷基、C1-4烷氧基、C2-5烷酰氧基或苯基-C1-4烷氧基基团，以及这些化合物的酸加合物和互变异构体。本发明的化合物显示出抑制胃酸分泌和细胞保护作用，可用于治疗胃肠系统溃疡。
• Imidazolderivate deren Herstellung und diese enthaltende Präparate
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0001279A1

  公开（公告）日：1979-04-04

  Verbindungen der Formel worin R1, R2, R3 und R4 je Wasserstoff oder R1 zusammen mit R1 und R' zusammen mit R' je eine zusätzliche Kohlenstoff-Kohlenstoff- Bindung, n dieZahl 0 oder 1, R5 Wasserstoff oder niederes Alkyl und X einen gegebenenfalls durch niederes Alkyl monosubstituierten 2-Pyridylrest, einen 2-Imidazolylrest, einen 2-Imidazolinylrest, einen 2-Thiazolylrest, einen 2-Thiazolinylrest, oder einen gegebenenfalls durch niederes Alkyl monosubstituierten 4(5)-Imidazolylrest bedeuten, und deren Säureadditionssalze hemmen die Magensekretion und können zur Behandlung von Magenulcera verwendet werden.

  式中的化合物 其中 R1、R2、R3 和 R4 各自为氢或 R1 连同 R1 和 R' 连同 R' 各自为额外的碳-碳键，n 为数字 0 或 1，R5 为氢或低级烷基，X 为可选被低级烷基单取代的 2-吡啶基、2-咪唑基、2-噻唑基、2-噻唑啉基或可选被低级烷基单取代的 4(5)- 咪唑基。2-咪唑啉基、2-噻唑基、2-噻唑啉基或任选由低级烷基单取代的 4(5)-咪唑基，它们的酸加成盐可抑制胃液分泌，可用于治疗胃溃疡。
• US4182766A
  申请人：——

  公开号：US4182766A

  公开（公告）日：1980-01-08