1,4-bis(azidomethyl)naphthalene | 190657-59-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-bis(azidomethyl)naphthalene
• CAS: 190657-59-1
• 化学式: C₁₂H₁₀N₆
• 分子量: 238.252
• InChiKey: LPTOTZRARCMAQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-bis(azidomethyl)naphthalene 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以60%的产率得到1,4-bis(aminomethyl)naphthalene
  参考文献：
  名称：

  Generation and in Situ Evaluation of Libraries of Poly(acrylic acid) Presenting Sialosides as Side Chains as Polyvalent Inhibitors of Influenza-Mediated Hemagglutination

  摘要：

  This paper describes a simple, microscale method for generating and evaluating libraries of derivatives of poly(acrylic acid) (pAA) that present mixtures of side chains that influence their biological activity. The method is based on the one-step conversion of poly(acrylic anhydride) (pAAn) to linear polymers presenting multiple units of R on side chains, pAA(R): the polymers are obtained by ultrasonication of a suspension of pAAn and aqueous RNH2 contained in a 250-mu L well of a microtiter plate. Using this method, derivatives of pAA having N-acetylneuraminic acid (NeuAc-L-NH2) as a side chain, pAA(NeuAc-L), were generated and assayed for ability to inhibit hemagglutination (HAI) of chicken erythrocytes by influenza virus A (X-31); the constant (KHAT) describing this inhibition is calculated on the basis of the concentration of NeuAc groups in solution, rather than the concentration of polymer molecules. Go-polymeric pAA(NeuAc-L-n; L-n=different linking groups) with a range of mole fractions of NeuAc-L-NH2 (chi(NeuAc-L)=0.02-0.11) exhibited HAI activities with K-i(HAI) values between 27 and 0.30 mu M. Using combinations of NeuAc-L-NH2 and one of 26 different primary amines RNH2, a variety of ter-polymeric pAA(NeuAc-L; R) (chi(Neu-Ac-L)similar to 0.05; chi(R) similar to 0.06) were also generated and assayed. Certain ter-polymers yielded values of K-i(HAI) that were lower by a factor of similar to 10(4) than that of the parent co-polymeric pAA(NeuAc-L): the most active inhibitor was pAA(NeuAc-L; L-3-(2'-naphthyl)alanine)) (K(i)(HAI)approximate to 0.05 mM). Typically, the incorporation of hydrophobic-especially aromatic-side chains enhanced activities. These polymers (pAA(NeuAc-L; R)) belong to a new class of polymeric, polyvalent sialosides that are potent inhibitors of the adsorption of influenza virus to erythrocytes. They were active with only low to moderate levels of incorporation of functional groups into the side chains: chi(NeuAc-L)similar to 0.05; chi(R) similar to 0.06.

  DOI：

  10.1021/ja963519x
• 作为产物：
  描述：

  1,4-双(溴甲基)萘 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到1,4-bis(azidomethyl)naphthalene
  参考文献：
  名称：

  Generation and in Situ Evaluation of Libraries of Poly(acrylic acid) Presenting Sialosides as Side Chains as Polyvalent Inhibitors of Influenza-Mediated Hemagglutination

  摘要：

  This paper describes a simple, microscale method for generating and evaluating libraries of derivatives of poly(acrylic acid) (pAA) that present mixtures of side chains that influence their biological activity. The method is based on the one-step conversion of poly(acrylic anhydride) (pAAn) to linear polymers presenting multiple units of R on side chains, pAA(R): the polymers are obtained by ultrasonication of a suspension of pAAn and aqueous RNH2 contained in a 250-mu L well of a microtiter plate. Using this method, derivatives of pAA having N-acetylneuraminic acid (NeuAc-L-NH2) as a side chain, pAA(NeuAc-L), were generated and assayed for ability to inhibit hemagglutination (HAI) of chicken erythrocytes by influenza virus A (X-31); the constant (KHAT) describing this inhibition is calculated on the basis of the concentration of NeuAc groups in solution, rather than the concentration of polymer molecules. Go-polymeric pAA(NeuAc-L-n; L-n=different linking groups) with a range of mole fractions of NeuAc-L-NH2 (chi(NeuAc-L)=0.02-0.11) exhibited HAI activities with K-i(HAI) values between 27 and 0.30 mu M. Using combinations of NeuAc-L-NH2 and one of 26 different primary amines RNH2, a variety of ter-polymeric pAA(NeuAc-L; R) (chi(Neu-Ac-L)similar to 0.05; chi(R) similar to 0.06) were also generated and assayed. Certain ter-polymers yielded values of K-i(HAI) that were lower by a factor of similar to 10(4) than that of the parent co-polymeric pAA(NeuAc-L): the most active inhibitor was pAA(NeuAc-L; L-3-(2'-naphthyl)alanine)) (K(i)(HAI)approximate to 0.05 mM). Typically, the incorporation of hydrophobic-especially aromatic-side chains enhanced activities. These polymers (pAA(NeuAc-L; R)) belong to a new class of polymeric, polyvalent sialosides that are potent inhibitors of the adsorption of influenza virus to erythrocytes. They were active with only low to moderate levels of incorporation of functional groups into the side chains: chi(NeuAc-L)similar to 0.05; chi(R) similar to 0.06.

  DOI：

  10.1021/ja963519x

文献信息

• Enantioselective Rh-Catalyzed Azide-Internal-Alkyne Cycloaddition for the Construction of Axially Chiral 1,2,3-Triazoles
  作者：Wen-Ting Guo、Bo-Han Zhu、Yi Chen、Jian Yang、Peng-Cheng Qian、Chao Deng、Long-Wu Ye、Long Li

  DOI：10.1021/jacs.2c01985

  日期：2022.4.20

  achieved for the construction of chiral skeletons containing 1,2,3-triazoles via transition-metal-catalyzed asymmetric azide–alkyne cycloaddition; however, most of them have been limited to terminal alkynes in the synthesis of central chirality via desymmetrization and dynamic/dynamic kinetic resolution. Enantioselective transition-metal-catalyzed azide-internal-alkyne cycloaddition is extremely limited

  通过过渡金属催化的不对称叠氮化物-炔烃环加成，构建含有 1,2,3-三唑的手性骨架取得了重大进展；然而，它们中的大多数仅限于通过去对称化和动态/动态动力学拆分合成中心手性的末端炔烃。对映选择性过渡金属催化的叠氮化物-内炔环加成反应极为有限。此外，通过过渡金属催化的不对称叠氮化物-内-炔烃环加成构建具有挑战性的五元（杂）联芳基轴向手性分子仍处于探索阶段。在此，我们首先报告了轴向手性 1,4,5-三取代 1,2,3-三唑的阻转选择性和原子经济合成，直接作为具有挑战性的五元阻转异构体的核心手性单元，通过内部炔烃和叠氮化物的对映选择性Rh催化叠氮化物-炔烃环加成（E-RhAAC）。该反应表现出优异的官能团耐受性，在温和条件下以中等至优异的产率（高达 99% 产率）和通常高至优异的对映选择性（高达 99%）锻造各种 C–C 轴向手性 1,2,3-三唑ee) 以及特定的区域控制。密度泛函理论 (DFT)
• [EN] POLYVALENT PRESENTER COMBINATORIAL LIBRARIES AND THEIR USES<br/>[FR] BIBLIOTHEQUES COMBINATOIRES DE PRESENTATION POLYVALENTE ET LEURS UTILISATIONS
  申请人：——

  公开号：WO1998047002A2

  公开（公告）日：1998-10-22

  [EN] The methods of the present invention provide for the synthesis and screening of combinatorial libraries of polyvalent presenters. The polyvalent presenters formed using the methods of the present invention generally have the formula (I);: R<1>-R<3>}m, wherein R<1> is a framework component, R<3> is a functional group component, and m is an integer having a value greater than ten and which is selected such that the presented functional groups can interact with a collection of greater than ten target binding sites. The framework component must b3e at least 10 KDa MW of sufficient means hydrodynamic radius to span the distance between adjacent receptors of the target, (ie.e, about 100 ANGSTROM or greater). These dimensions permit the plurality of functional groups attached to the framework to simultaneously bind to the target receptors (e.g., cell surface receptors). In some embodiments, the polyvalent presenters have the formula (II): R<1>-R<2>(-R<3>)m}n, wherein R<1> and R<3> area s defined above, m is an integer having a value greater than ten and which is selected such that the presented functional groups can interact with a collection of greater than ten target binding sites. In other embodiments, ancillary groups are prsent in the polyvalent presenters of the present invention, the ancillary group imparting or latering a characteristic(s) of the polyvalent presenter. Properties which can be imparted and-or modified include, for example, solubility (in water, fats, lipids, biological fluids, etc.), hydrophobicity, hydrophilicity, charge framework flexibility, antigenicity, molecular size, molecular weight, biocompatibility, immunogenicity, stability, in vivo half-life, in vivo distribution, strength of binding to the polyvalent target, etc.
  [FR] L'invention concerne des procédés de synthèse et de sélection de bibliothèques combinatoires de présentateurs polyvalents. Les présentateurs polyvalents de l'invention sont de la formule (I); R'<-R?3>}m dans laquelle R<1> est un élément de charpente, R<3> est un élément d'un groupe fonctionnel, et m est un entier de valeur supérieure à dix sélectionné de telle manière que les groupes fonctionnels présentés peuvent interagir avec un ensemble de plus de dix sites de fixation cibles. L'élément de charpente doit être au moins égal à 10 KDa MW de rayon hydrodynamique moyen suffisant pour couvrir la distance entre des récepteurs adjacents de la dible (environ 100 ANGSTROM ou plus par exemple). Ces dimensions permettent à la pluralité de groupes fonctionnels fixés à la charpente de se lier simultanément aux récepteurs cibles (récepteurs de la surface cellulaire). Dans certains aspects, les présentateurs polyvalents sont de la formule (II): R<1>-R<2>(-R<3>)m}n dans laquelle R<1> et R<3> sont tels que définis ci-dessus, m est un entver de valeur égale ou supérieure à un, R<2> un groupe espaceur ou lieur et "n" est un entier de valeur supérieure à dix sélectionné de telle manière que les groupes fonctionnels présentés peuvent interagir avec un ensemble de plus de dix sites de fixation cibles. Dans d'autres aspects, des groupes secondaires sont inclus dans les présentateurs polyvalents et apportent ou modifient une ou des caractéristiques du présentateur polyvalent. Les caractéristiques suivantes figurent parmi celles qui peuvent être apportées ou modifiées: solubilité (dans l'eau, les matières grasses, les lipides, les fluides biologiques, etc.), hydrophobie, hydrophilie, capacité de charge, souplesse de la charpente, antigénie, taille moléculaire, poids moléculaire, biocompatibilité, immunogénicité, stabilité, demi-vie in vivo, répartition in vivo, force de liaison à la cible polyvalente, etc.