4-吲哚吡啶-2,6-二羧酸 | 506423-80-9

• 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: 4-吲哚吡啶-2,6-二羧酸
• 英文名称: 4-iodopyridine-2,6-dicarboxylic acid
• CAS: 506423-80-9
• 化学式: C₇H₄INO₄
• 分子量: 293.018
• InChiKey: CIYYPWOUZPEAHS-UHFFFAOYSA-N

物化性质

• 沸点：
  526.4±50.0 °C(Predicted)
• 密度：
  2.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-吲哚吡啶-2,6-二羧酸 在 sodium tetrahydroborate 、 selenium(IV) oxide 、 硫酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 26.5h， 生成 4-碘-2,6-吡啶二甲醛
  参考文献：
  名称：

  具有扩展 π 系统的凹面吡啶

  摘要：

  新的 4-取代凹吡啶 1b-d 已被合成为前体，以允许吡啶 π 系统的扩展。以 Sonogashira 偶联作为关键合成步骤，4-碘吡啶 1c 与苯乙炔 (11) 偶联得到 1g，产率为 77%。由于其共轭 π 系统，新的凹形吡啶 1g 在 λmax1 = 286 nm 和 λmax2 = 303 nm 处具有紫外吸收最大值，其中 ϵmax1 = 43300 Lmol−1cm−1 和 ϵmax2 = 39300 Lmol−1cm−1，分别允许其潜力作为传感器的应用。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0690(200211)2002:21<3680::aid-ejoc3680>3.0.co;2-4
• 作为产物：
  描述：

  4-氯吡啶-2,6-二羧酸 在 sodium hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 4-吲哚吡啶-2,6-二羧酸
  参考文献：
  名称：

  Effects of a halogenated G-quadruplex ligand from the pyridine dicarboxamide series on the terminal sequence of XpYp telomere in HT1080 cells

  摘要：

  Non-canonical four-stranded structures called G-quadruplexes can form among telomere repeats during its replication. Small molecule ligands able to interact and to stabilize G-quadruplexes were shown to disrupt the binding of essential telomeric components, such as POT] and to trigger a telomeric dysfunction associated with a delayed growth arrest in tumor cells. We describe here the chemical synthesis and the G-quadruplex binding properties of three halogenated analogs of the 360A ligand that belongs to the 2,6 pyridine dicarboxamide series. 360A is now commonly used as a benchmark both for biophysical and cellular assays as this compound was shown to display a potent affinity and selectivity for telomeric G-quadruplex DNA over duplex DNA and to induce delayed growth inhibition in HT1080 tumor cell line. Two biophysical assays indicate that, in most cases, the presence of the halogen atom seems to slightly improve the interaction with the telomeric quadruplex. For stability reasons, the bromo derivative (360A-Br) was selected for the cellular assays. Since POT1 participates to the fine tuning of the C-strand end resection during telomere replication, we investigated the effect of 360A-Br to alter the terminal nucleotide composition of XpYp telomere in HT1080 cells using C-STELA. HT1080 cells treated for up to 24 days with 360A-Br presented some minor but significant variations of C-strand terminal nucleotide composition, also observed with a partial siRNA depletion of POT1. The relevance of these minor modifications of the telomeric C-strand resection induced by 360A-Br in HT1080 cells are discussed. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2012.07.003

文献信息

• Copper(<scp>ii</scp>)-directed synthesis of neutral heteroditopic [2]rotaxane ion-pair host systems incorporating hydrogen and halogen bonding anion binding cavities
  作者：Asha Brown、Katrina M. Mennie、Owen Mason、Nicholas G. White、Paul D. Beer

  DOI：10.1039/c7dt02832f

  日期：——

  Neutral heteroditopic [2]rotaxane ion-pair host systems were synthesised via a Cu(II) directed passive metal template strategy. Each rotaxane contains discrete, axle-separated interlocked binding sites for a guest anion and a transition metal countercation. The anion binding sites are composed of convergent X–H (X = C, N) hydrogen bond donor groups, or mixed X–H and C–I hydrogen and halogen bond donor

  通过Cu（II）定向的被动金属模板策略合成了中性异位双[2]轮烷离子对宿主系统。每个轮烷均包含离散的，轴分隔的互锁的结合位点，用于客体阴离子和过渡金属抗衡阳离子。阴离子结合位点由会聚的X–H（X = C，N）氢键供体基团，或混合的X–H和C–1氢和卤素键供体基团组成，而等效的三维阵列的胺，吡啶羰基氧供体基团构成过渡金属结合位点。在CDCl 3 / CD 3 OD或CDCl 3 / CD 3 OD / D 2中的1 H NMR滴定实验O溶剂混合物表明，异位[2]轮烷主系统能够在存在共键合的Zn（II）阳离子的情况下进行协同阴离子识别。
• SUBSTITUTED PYRIDINE COMPOUNDS AS PESTICIDES
  申请人：Bayer CropScience Aktiengesellschaft

  公开号：US20190053492A1

  公开（公告）日：2019-02-21

  The present invention relates to novel substituted pyridine compounds of the formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , V 1 , V 2 and Q 1 have the definitions given in the description, and to the use thereof as acaricides and insecticides for control of animal pests, particularly arthropods and especially insects and arachnids, and to processes and intermediates for preparation thereof.

  本发明涉及一种新型的取代吡啶化合物，其化学式为（I），其中R1、R2、R3、R4、R5、R6、V1、V2和Q1具有描述中给定的定义，并且作为杀虫剂和杀虫剂用于控制动物害虫，特别是节肢动物，尤其是昆虫和蜘蛛，以及其制备的过程和中间体。
• Efficient Formation of Luminescent Lanthanide(III) Complexes by Solid‐Phase Synthesis and On‐Resin Screening
  作者：Tatsuya Nakamura、Shin Mizukami、Miho Tanaka、Kazuya Kikuchi

  DOI：10.1002/asia.201300759

  日期：2013.11

  measurements of luminescent lanthanide complexes have advantages in biological assays and high‐throughput screening, owing to their high sensitivity. In spite of the recent advances in their energy‐transfer mechanism and molecular‐orbital‐based computational molecular design, it is still difficult to estimate the quantum yields of new luminescent lanthanide complexes. Herein, solid‐phase libraries of

  发光镧系元素络合物的时间分辨发光测量因其灵敏度高而在生物学分析和高通量筛选中具有优势。尽管在能量转移机理和基于分子轨道的计算分子设计方面取得了最新进展，但仍难以估计新型发光镧系元素络合物的量子产率。在此，通过酰胺缩合和Pd催化的偶联反应制备了发光镧系元素络合物的固相库，并使用酶标仪对它们的发光性质进行了筛选。固相文库的时间分辨发光强度与使用液相化学合成的相应配合物的时间分辨发光强度之间观察到良好的相关性。III，Eu III和Tb III发光。因此，固相组合合成与树脂上的筛选相结合，导致发现了多种发光敏化剂。
• Toward an Artificial Oxidative DNA Photolyase
  作者：Mickaël Pauvert、Patrick Laine、Marco Jonas、Olaf Wiest

  DOI：10.1021/jo0354600

  日期：2004.1.1

  The design, synthesis, structure, and binding affinity of two dioptic receptors for the selective molecular recognition of the cis,syn cyclobutane pyrimidine dimer are reported. The design is based on two 2,6-di(acetamino)pyridine recognition units that are covalently linked via triple bonds to an anthraquinone functional spacer unit. The convergent synthesis uses a modified Sonogashira reaction involving

  报道了用于选择性分子识别顺式，顺式环丁烷嘧啶二聚体的两个屈光受体的设计，合成，结构和结合亲和力。该设计基于两个2,6-二（乙酰氨基）吡啶识别单元，它们通过三键共价连接至蒽醌功能性间隔基单元。收敛合成使用了涉及锌转金属的修饰的Sonogashira反应作为关键步骤。受体之一的晶体结构揭示了一种超分子一维聚合物，该聚合物具有较强的相互作用，该相互作用由形状自互补，π堆积和相邻分子之间的氢键介导。相邻链之间的氢键强制平行取向，从而导致高极性化合物的非中心对称晶体结构。受体的缔合常数为K a = 1.0×10 3 M - 1，具有顺式，顺式嘧啶二聚体，而反式，顺式异构体的结合力弱约1个数量级。
• Graf, Journal fur praktische Chemie (Leipzig 1954), 1937, vol. <2> 148, p. 13,16
  作者：Graf

  DOI：——

  日期：——