m-phenylazobenzoic acid | 37790-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: m-phenylazobenzoic acid
• 英文别名: (E)-3-(phenyldiazenyl)benzoic acid
• CAS: 37790-19-5
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: PSIKAQNVARWEFI-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.02
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  m-phenylazobenzoic acid 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 氯化亚砜 、 sodium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(diethylcarbamoyl)-4-(phenyldiazenyl)benzoic acid
  参考文献：
  名称：

  偶氮苯的化学选择性去质子化锂化：反应和机理

  摘要：

  而标准强碱（n -BuLi，s -BuLi / TMEDA，n -BuLi / t -BuOK，TMPMgCl·LiCl和LDA）会降低母体偶氮苯的N═N键（Y = H），芳香族H→Li当偶氮化合物的苯残基中存在合适的锂化导向剂（Y = OMe，CONEt 2，F）时，LTMP发生置换。该方法允许直接获得新的取代的偶氮苯。

  DOI：

  10.1021/jo500230q
• 作为产物：
  描述：

  trans-azobenzene-3-carboxylic acid methyl ester 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以97%的产率得到m-phenylazobenzoic acid
  参考文献：
  名称：

  Photopharmacological Manipulation of Mammalian CRY1 for Regulation of the Circadian Clock

  摘要：

  DOI：

  10.1021/jacs.0c12280

文献信息

• Azobenzene-containing photoswitchable proteasome inhibitors with selective activity and cellular toxicity
  作者：Beatriz Blanco、Kathryn A. Palasis、Alaknanda Adwal、David F. Callen、Andrew D. Abell

  DOI：10.1016/j.bmc.2017.06.011

  日期：2017.10

  A series of azobenzene-containing peptidic boronate esters was prepared and the activity of the thermally adapted states (TAS), enriched in trans isomer, and the photostationary states (PSS), enriched in cis isomer, for each compound were evaluated against β5 and β1 proteasome subunits. Compounds with a sterically demanding phenyl-substituted azobenzene at P2 (4c), and a less sterically demanding unsubstituted

  制备了一系列含偶氮苯的肽硼酸酯，并针对每种化合物针对β5和β1评估了富含反式异构体的热适应态（TAS）和富含顺式异构体的光平稳态（PSS）的活性。蛋白酶体亚基。在P2（4c）处具有空间要求的苯基取代的偶氮苯，而在N端（5a）具有较低空间要求的未取代的偶氮苯的化合物显示出两种状态之间最大的活性差异。在这两种情况下，活性更高的反式富集的TAS的活性均与硼替佐米和地兰佐米相当。此外，富含顺式的4c抑制了乳腺癌和结直肠癌细胞系中的肿瘤生长。值得注意的是，最初的4c反式富集TAS对非恶性MCF-10A细胞没有细胞毒性。
• Optical Control of Mitosis with a Photoswitchable Eg5 Inhibitor
  作者：Anna C. Impastato、Andrej Shemet、Nynke A. Vepřek、Gadiel Saper、Henry Hess、Lu Rao、Arne Gennerich、Dirk Trauner

  DOI：10.1002/anie.202115846

  日期：2022.2.21

  The optical control of a mitotic kinesin, Eg5, was achieved through an azobenzene analog of EMD-534085. Under UV light conditions, HeLa cells undergo mitotic arrest, as evidenced by the formation of a monopolar spindle.

  有丝分裂驱动蛋白 Eg5 的光学控制是通过 EMD-534085 的偶氮苯类似物实现的。在紫外线条件下，HeLa 细胞发生有丝分裂停滞，单极纺锤体的形成证明了这一点。
• First-in-Class Colchicine-Based Visible Light Photoswitchable Microtubule Dynamics Disrupting Agent
  作者：Filip Borys、Piotr Tobiasz、Hanna Fabczak、Ewa Joachimiak、Hanna Krawczyk

  DOI：10.3390/cells12141866

  日期：——

  Compounds that disrupt microtubule dynamics, such as colchicine, paclitaxel, or Vinca alkaloids, have been broadly used in biological studies and have found application in clinical anticancer medications. However, their main disadvantage is the lack of specificity towards cancerous cells, leading to severe side effects. In this paper, we report the first synthesis of 12 new visible light photoswitchable

  破坏微管动力学的化合物，如秋水仙碱、紫杉醇或长春花生物碱，已广泛用于生物学研究，并已在临床抗癌药物中得到应用。然而，它们的主要缺点是缺乏针对癌细胞的特异性，导致严重的副作用。在本文中，我们首次合成了 12 种新型可见光光控秋水仙碱微管抑制剂 AzoCols。在获得的化合物中，两种光开关在癌细胞系（HCT116和MCF-7）中表现出光依赖性细胞毒性。最有前途的化合物显示出效力增加了近两倍。此外，在无细胞测定中纯化的微管蛋白聚合的不同抑制作用和通过免疫荧光成像可视化的光依赖性微管组织破坏揭示了微管光开关去稳定剂的作用机制。所提出的结果为合成和开发一类新型光开关秋水仙碱微管聚合抑制剂奠定了基础。
• Structure requirements for anaerobe processing of azo compounds: Implications for prodrug design
  作者：Jason Gavin、Juan F. Marquez Ruiz、Kinga Kedziora、Henry Windle、Dermot P. Kelleher、John F. Gilmer

  DOI：10.1016/j.bmcl.2012.10.014

  日期：2012.12

  This Letter generalizes the metabolism of the azo class of compounds by Clostridium perfringens, an anaerobe found in the human colon. A recently reported 5-aminosalicylic acid-based prednisolone prodrug was shown to release the drug when incubated with the bacteria, while the para-aminobenzoic acid (PABA) based analogue did not. Instead, it showed a new HPLC peak with a relatively close retention time to the parent which was identified by LCMS as the partially reduced hydrazine product. This Letter investigates azoreduction across a panel of substrates with varying degrees of electronic and steric similarity to the PABA-based compound. Azo compounds with an electron donating group on the azo-containing aromatic ring showed immediate disproportionation to their parent amines without any detection of hydrazine intermediates by HPLC. Compounds containing only electron withdrawing groups are partially and reversibly reduced to produce a stable detectable hydrazine. They do not disproportionate to their parent amines, but regenerate the parent azo compound. This incomplete reduction is relevant to the design of azo-based prodrugs and the toxicology of azo-based dyes. (C) 2012 Elsevier Ltd. All rights reserved.
• Azobenzene-Containing, Peptidyl α-Ketoesters as Photobiological Switches of α-Chymotrypsin
  作者：Andrew J Harvey、Andrew D Abell

  DOI：10.1016/s0040-4020(00)00883-8

  日期：2000.12

  Three photoswitchable, peptidomimetic inhibitors of oc-chymotrypsin have been synthesised. The compounds comprise an azobenzene, an alpha -ketoester and L-phenylalanine. The compounds were photoisomerised to give enriched states of the (E) and (Z) isomers and these states were assayed against alpha -chymotrypsin. The inhibitors were shown to be moderately active with switching ability of between two- and three-fold between the two isomer-enriched states. The behaviour of the inhibitors in solution was examined; specifically, their hydration and configurational stability. (C) 2000 Elsevier Science Ltd. All rights reserved.

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