α-(2-pyridyl)benzyl chloride | 40473-17-4

• 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: α-(2-pyridyl)benzyl chloride
• 英文别名: 2-(chloro(phenyl)methyl)pyridine；2-[chloro(phenyl)methyl]pyridine
• CAS: 40473-17-4
• 化学式: C₁₂H₁₀ClN
• 分子量: 203.671
• InChiKey: WNPOXIFIUWYVMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-(2-pyridyl)benzyl chloride 在 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 4.0h， 生成 1-phenyl-4-4-[phenyl(2-pyridyl)methyl]piperazino-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of pyrazolo[3,4-d]pyrimidines: a novel class of potent enterovirus inhibitors

  摘要：

  A series of pyrazolo[3,4-d]pyrimidines were synthesized. and their antiviral activity was evaluated in a plaque reduction assay. It is very interesting that this class of compounds provide remarkable evidence that they are very specific for human enteroviruses, in particular, coxsackieviruses. Some derivatives proved to be highly effective in inhibiting enterovirus replication at nanomolar concentrations. SAR studies revealed that the phenyl group at the N-I position and the hydrophobic diarylmethyl group at the piperazine largely influenced the in vitro antienteroviral activity of this new class of potent antiviral agents. It was found that the pyrazolo[3,4-d]pyrimidines with a thiophene substituent, such as compounds 20 24, in general exhibited high activity against coxsackievirus B3 (IC50 = 0.063-0.089 muM) and moderate activity against enterovirus 71 (IC50 = 0.32-0.65 muM) with no apparent cytotoxic effect toward RD (rhabdomyosarcoma) cell lines (CC50>25 muM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.092
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氯化亚砜 、 苯 作用下， 生成 α-(2-pyridyl)benzyl chloride
  参考文献：
  名称：

  Preparation of piperazine derivatives

  摘要：

  公开号：

  US02861072A1

文献信息

• Synthesis and gastric antisecretory activity of N-cyano-N'-(phenyl-pyridinylmethyl)guanidine derivatives.
  作者：KATSUTOSHI SHIMADA、HIDEAKI FUJISAKI、KIYOSHI OKETANI、MANABU MURAKAMI、TADAO SHOJI、TSUNEO WAKABAYASHI、KOICHIRO UEDA、KIICHI EMA、KAZUNORI HASHIMOTO、SATORU TANAKA

  DOI：10.1248/cpb.32.4893

  日期：——

  N-Alkyl-N'-cyano-N"-(substituted phenyl-pyridinylmethyl) guanidine derivatives were synthesized and tested for inhibitory activity against gastric secretion in rats. Several of the compounds synthesized showed an inhibiting activity as potent as that of cimetidine against basal gastric secretion but showed less potent activity than cimetidine against histamine-stimulated gastric secretion. Some structure-activity relationships are discussed.

  N-烷基-N'-氰基-N"-(取代苯基吡啶甲基)胍衍生物被合成并测试了对大鼠胃分泌的抑制活性。合成的化合物中，有几个展现了对基础胃分泌的抑制活性，与西咪替丁相当，但在对抗组胺刺激的胃分泌方面，活性不如西咪替丁。还讨论了一些结构-活性关系。
• Benzylpiperazine derivatives. II. Syntheses and cerebral vasodilating activities of 1-((3-alkyl-3-hydroxy-3-phenyl)propyl)-4-benzylpiperazine derivatives.
  作者：HIROSHI OHTAKA、YOSHIAKI FUJIMOTO、KENJI YOSHIDA、TOSHIRO KANAZAWA、KEIZO ITO、GORO TSUKAMOTO

  DOI：10.1248/cpb.35.2782

  日期：——

  Analogs of 1-[ (3-alkyl-3-hydroxy-3-phenyl) propyl]-4- (2, 3, 4-trimethoxybenzyl) piperazine (1) were prepared and tested for cerebral vasodilating activity. It was found that the potency depends positively on the number of methoxyl groups on the benzyl moiety, and the homopiperazine analogs seem to be equipotent to the corresponding piperazines. From the standpoints of potency and ease of synthesis, 8k was selected for further study. Further analogs, which have various substituents in place of the benzyl moiety of 8k, were prepared and tested for cerebral vasodilating activity. These analogs were less potent than 8k. It was suggested that the benzyl moiety of 8k plays an important role in the high cerebral vasodilating activity.

  1-[ (3-烷基-3-羟基-3-苯基)丙基]-4- (2, 3, 4-三甲氧基苯基)哌嗪（1）的类似物被制备并测试了其脑血管扩张活性。研究发现，活性强度与苄基部分上的甲氧基团数量呈正相关，而同脉哌嗪类的类似物似乎与相应的哌嗪类同样具有活性。从活性和合成简便性来看，选定了8k进行进一步研究。随后制备了在8k的苄基部分替换为各种取代基的其他类似物，并测试了其脑血管扩张活性。这些类似物的活性均低于8k。研究者认为，8k的苄基部分在其高脑血管扩张活性中起着重要作用。
• Nickel-Catalyzed Formal Aminocarbonylation of Secondary Benzyl Chlorides with Isocyanides
  作者：Yun Wang、Wenyi Huang、Chenglong Wang、Jingping Qu、Yifeng Chen

  DOI：10.1021/acs.orglett.0c01284

  日期：2020.6.5

  versatile feedstocks in synthetic chemistry, widely existing in drug molecules and natural products. Herein, we disclose a nickel-catalyzed formal aminocarbonylation of secondary benzyl chlorides with isocyanides yielding α-substituted phenylacetamide with steric hindrance, which is synthetically challenging via palladium-catalyzed aminocarbonylation. The reaction features wide functional group tolerance

  苯乙酰胺代表了合成化学中的多种原料，广泛存在于药物分子和天然产物中。在本文中，我们公开了用异氰酸酯对仲苄基氯进行镍催化的正式氨基羰基化反应，产生具有位阻的α-取代的苯乙酰胺，这在钯催化的氨基羰基化反应中是具有挑战性的。该反应在温和条件下具有宽泛的官能团耐受性，突出了各种芳族​​卤化物（-Cl，-Br，-I）和杂芳环（吡啶和吡嗪）的耐受性。
• Palladium complexes of bidentate pyridine<i>N</i>-heterocyclic carbenes: Optical resolution, antimicrobial and cytotoxicity studies
  作者：Kar Bee Choo、Wee Li Mah、Sui Mae Lee、Wai Leng Lee、Yuen Lin Cheow

  DOI：10.1002/aoc.4377

  日期：2018.8

  to that, cytotoxic activities of the Pd NHC complexes were also evaluated against three human cancer cell lines, namely breast (MCF‐7), colon (HCT116) and oral (H103) cancer cells, using a standard MTT assay. Upon coordination to palladium, the Pd NHC complexes show significant antimicrobial activities with minimum inhibitory concentrations in the micromolar range, and they are cytotoxic to the tested

  一系列带有各种翼尖取代基（R =甲基，苯基和叔丁基）的双齿吡啶官能化钯N杂环卡宾（Pd NHC）配合物-丁基）已被合成并评估了其作为抗微生物剂和抗增殖药物候选物的潜在生物医学应用。将获得的Pd NHC复合物应用于标准肉汤微量稀释测定法中，以测定其对13种病原微生物菌株的抗菌活性。除此之外，还使用标准MTT分析法评估了Pd NHC复合物对三种人类癌细胞系，即乳腺癌（MCF-7），结肠（HCT116）和口腔（H103）癌细胞的细胞毒性活性。与钯配位后，Pd NHC复合物显示出显着的抗菌活性，且在微摩尔范围内具有最低抑制浓度，并且对经IC 50检测的癌症具有细胞毒性范围从13到38μM。已发现影响翼尖取代基和旋光异构性两者对复合物生物活性的证据。
• Synthesis and Characterisation of a Novel Chiral Bidentate Pyridine‐N‐Heterocyclic Carbene‐Based Palladacycle
  作者：Minyi Chiang、Yongxin Li、Deepa Krishnan、Pullarkat Sumod、Kim Hong Ng、Pak‐Hing Leung

  DOI：10.1002/ejic.200901142

  日期：2010.3

  A novel chiral six-membered bidentate pyridine-N-heterocyclic carbene palladacycle was prepared via optical resolution of the racemic palladacycle. This is the first successful demonstration of the synthesis of a chiral carbene palladacycle via fractional crystallization of its chiral amino acid derivatives. Upon formation of (R C ,S C ) and (S C ,S C )-phenylalanate derivatives, the (R C ,S C )-phenylalanate

  通过外消旋钯环的光学拆分制备了一种新型手性六元双齿吡啶-N-杂环卡宾钯环。这是通过手性氨基酸衍生物的分级结晶合成手性卡宾钯环的首次成功证明。在形成 (RC ,SC ) 和 (SC ,SC )-苯丙酸酯衍生物后，(RC ,SC )-苯丙酸酯非对映异构体自发结晶出来。然后可以通过随后在 HCl 水溶液的存在下将手性氨基酸辅助剂从它们各自的非对映异构体上裂解来获得光学活性的 (R)-和 (S)-二氯钯环。(R)-和(S)-钯环的绝对构型通过X-射线衍射研究确定。