3′-bromo-3,4′-bipyridine | 1356406-39-7

• 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: 3′-bromo-3,4′-bipyridine
• 英文别名: 3’-bromo-3,4’-bipyridine；3'-bromo-3,4'-bipyridine；3'-bromo-[3,4']bipyridinyl；3-Bromo-4-(pyridin-3-yl)pyridine；3-bromo-4-pyridin-3-ylpyridine
• CAS: 1356406-39-7
• 化学式: C₁₀H₇BrN₂
• mdl: MFCD22379718
• 分子量: 235.083
• InChiKey: DUSREXJLHQEODB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3′-bromo-3,4′-bipyridine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 3-([3,4′-bipyridin]-3′-yl)prop-2-yn-1-amine trihydrochloride
  参考文献：
  名称：

  3-炔基和3-杂芳族取代的吡啶甲烷甲胺的4-位的鉴定为关键修饰位点，可提高细胞色素P-450 2A6抑制的效力和选择性。

  摘要：

  在美国，抽烟导致五分之一的死亡。已经开发了一种特定的细胞色素P450 2A6抑制剂（CYP2A6），它是人类主要的尼古丁代谢酶，可用于戒烟。为了进一步改善CYP2A6的结构活性关系，将先前合成的3-炔基和3-杂芳族取代的吡啶甲胺用作前导化合物。进行等位吡啶取代和吡啶环周围所有可用位置的甲基附接，以识别会增加CYP2A6抑制力的修饰，从而导致4g（IC 50= 0.055 mM）作为主要类似物。对强效化合物的CYP选择性，人肝微粒体半衰期以及是否符合5条规则进行了评估。顶尖的化合物（即6i，IC 50 = 0.017 mM，半衰期> 120分钟）已准备好进一步发展，作为戒烟和戒烟的治疗方法。

  DOI：

  10.1021/acs.jmedchem.8b00084
• 作为产物：
  描述：

  3,4-二溴吡啶 、 3-吡啶硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以42%的产率得到3′-bromo-3,4′-bipyridine
  参考文献：
  名称：

  Structural Characterizations of Oligopyridyl Foldamers, α-Helix Mimetics

  摘要：

  Protein-protein interactions are central to many biological processes, from intracellular communication to cytoskeleton assembly, and therefore represent an important class of targets for new therapeutics. The most common secondary structure in natural proteins is an alpha-helix. Small molecules seem to be attractive candidates for stabilizing or disrupting protein protein interactions based on alpha-helices. In our study, we assessed the ability of oligopyridyl scaffolds to mimic the alpha-helical twist. The theoretical as well as experimental studies (X-ray diffraction and NMR) on conformations of bipyridines in the function of substituent and pyridine nitrogen positions were carried out. Furthermore, the experimental techniques showed that the conformations observed in bipyridines are maintained within a longer oligopyridyl scaffold (quaterpyridines). The alignment of the synthesized quaterpyridine with two methyl substituents showed that it is an alpha-helix foldamer; their methyl groups overlap very well with side chain positions, i and i + 3, of an ideal alpha-helix.

  DOI：

  10.1021/ci200424a

文献信息

• [EN] PHARMACEUTICAL AGENTS FOR USE IN SMOKING AND TOBACCO CESSATION<br/>[FR] PRODUITS PHARMACEUTIQUES DESTINÉS À ÊTRE UTILISÉS POUR L'ARRÊT DU TABAC ET LE SEVRAGE TABAGIQUE
  申请人：UNIV WASHINGTON STATE

  公开号：WO2020010242A1

  公开（公告）日：2020-01-09

  The present disclosure describes novel compounds and compositions that reduce nicotine mediated cravings in humans. In embodiments, the novel compounds blocking CYP2A6-meditated nicotine metabolism thereby reducing the need for additional nicotine. Leading to a desirable treatment option in reducing nicotine craving which does not exacerbate the sympathetic response rate caused by the abused substance and which has favorable pharmacodynamics effects.

  本公开描述了一种新型化合物和组合物，可以减少人类体内尼古丁介导的渴望。在实施例中，这些新型化合物通过阻断CYP2A6介导的尼古丁代谢来减少对额外尼古丁的需求。从而导致一种理想的治疗选择，可以减少尼古丁渴望，而不会加剧滥用物质引起的交感反应速率，并具有良好的药效学效果。
• Pyrazole Compounds for Controlling Invertebrate Pests
  申请人：Soergel Sebastian

  公开号：US20130253012A1

  公开（公告）日：2013-09-26

  The present invention relates to a method for controlling invertebrate pests, in particular arthropod pests and nematodes, by using pyrazole compounds of formula I and the salts thereof, the tautomers thereof, the N-oxides thereof and the salts of the tautomers or N-oxides thereof, wherein X is N or CH, Y is N or CH, Z is N or CH, provided that either only one of X, Y and Z is N or only two adjacent groups of X, Y and Z are N; and wherein Q is a bivalent 5- or 6-membered carbocyclic radical or a 5- or 6-membered heterocyclic radical having one heteroatom moiety which is selected from the group consisting of O, S, N or N—R QN as ring member and 0, 1 or 2 further heteroatom moieties N as ring members, wherein 0, 1, 2 or 3 of the ring members that are carbon atoms may carry a radical R Q , provided that the pyrazole radical and the 6-membered heteroaromatic radical are bound in ortho- or meta-position of Q with respect to each other, if Q is a 6-membered radical; and wherein R A , if present, is C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl or the like; n is 0, 1 or 2; R N is C 1 -C 3 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl or the like; R t and R u are independently of each other selected from hydrogen, methyl and the like; R QN is hydrogen, C 1 -C 4 -alkyl or the like; R Q is hydrogen, halogen, C 1 -C 4 -alkyl or the like. The present invention further relates to a method for protecting plant propagation material and/or the plants which grow therefrom, to plant propagation material, comprising at least one compound of formula I, their salts or N-oxides, and to pyrazole compounds of formula I.

  本发明涉及一种使用式I的吡唑化合物及其盐、互变异构体、N-氧化物及其互变异构体或N-氧化物的盐，控制无脊椎动物害虫，特别是节肢动物害虫和线虫的方法，其中X为N或CH，Y为N或CH，Z为N或CH，只有X、Y和Z中的一个是N或仅有相邻的两个X、Y和Z中的一个是N；Q为二价的5-或6-成员的碳环或一个5-或6-成员的杂环基团，其中一个杂原子基团被选择为O、S、N或N-RQ，作为环成员，0、1或2个进一步的杂原子基团N作为环成员，其中0、1、2或3个是碳原子的环成员可能携带一个基团RQ，只要吡唑基团和6-成员杂环芳基团在Q的正交或间位于彼此相对位置，如果Q是6-成员基团；RA如果存在，则为C1-C3烷基、C1-C3卤代烷基或类似物；n为0、1或2；RN为C1-C3烷基、C1-C2卤代烷基、C1-C2-烷氧基-C1-C2-烷基或类似物；Rt和Ru独立地选择自氢、甲基等；RQN为氢、C1-C4烷基或类似物；RQ为氢、卤素、C1-C4烷基或类似物。本发明还涉及一种保护植物繁殖材料和/或从中生长的植物的方法，包括至少一种式I化合物、它们的盐或N-氧化物，以及式I的吡唑化合物的植物繁殖材料。
• [EN] PYRAZOLE COMPOUNDS FOR CONTROLLING INVERTEBRATE PESTS<br/>[FR] COMPOSÉS DE PYRAZOLE POUR LA LUTTE CONTRE DES ANIMAUX NUISIBLES INVERTÉBRÉS
  申请人：BASF SE

  公开号：WO2012076704A3

  公开（公告）日：2012-08-02
• PYRAZOLE COMPOUNDS FOR CONTROLLING INVERTEBRATE PESTS
  申请人：BASF SE

  公开号：EP2648518A2

  公开（公告）日：2013-10-16
• PHARMACEUTICAL AGENTS FOR USE IN SMOKING AND TOBACCO CESSATION
  申请人：Washington State University

  公开号：US20210276987A1

  公开（公告）日：2021-09-09

  The present disclosure describes novel compounds and compositions that reduce nicotine mediated cravings in humans. In embodiments, the novel compounds blocking CYP2A6-meditated nicotine metabolism thereby reducing the need for additional nicotine. Leading to a desirable treatment option in reducing nicotine craving which does not exacerbate the sympathetic response rate caused by the abused substance and which has favorable pharmacodynamics effects.