(2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl) phenyl)arsonic acid | 1288981-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl) phenyl)arsonic acid
• 英文别名: (2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)phenyl)arsonic acid；[2-[2-(2,4-dioxopentan-3-ylidene)hydrazinyl]phenyl]arsonic acid
• CAS: 1288981-02-1
• 化学式: C₁₁H₁₃AsN₂O₅
• 分子量: 328.156
• InChiKey: JEBOIDNIKMKFSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.81
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  116.06
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl) phenyl)arsonic acid 、 copper(II) nitrate trihydrate 以 水 为溶剂， 以54%的产率得到
  参考文献：
  名称：

  铜（ii）与3-（邻位取代的苯基肼基）戊烷-2,4-二酮的配合物：环己烷氧化的合成，性质和催化活性†

  摘要：

  铜（II）与3-苯基肼基戊烷-2,4-二酮X-2-C 6 H 4 –NHN C {C（O）CH 3 } 2在邻位带有取代基的反应[X = OH（H 2 L 1）1，AsO 3 H 2（H 3 L 2）2，Cl（HL 3）3，SO 3 H（H 2 L 4）4，COOCH 3（HL 5）5，COOH（H2 L 6） 6，NO 2（HL 7） 7或H（HL 8） 8 ]导致各种络合物，包括单体[CuL 4（H 2 O） 2 ]·H 2 O 10，[CuL 4（ ħ 2 O） 2 ] 11和[铜（HL 4） 2（H 2 O） 4 ] 12，二聚物[Cu 2（H 2 O） 2（μ-HL 2）2 ] 9和聚合物[Cu（μ-L 6）] Ñ ] 13分的，常带有两个稠合的六元metallacycles。配合物10–12可以相互转化，具体取决于pH和温度，而Cu（ II）与4（在存在氰基胍 或者 咪唑（IM），得到单体化合物[铜（H

  DOI：

  10.1039/c0dt01527j
• 作为产物：
  描述：

  2-氨基苯胂酸 、 乙酰丙酮 在 盐酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以67%的产率得到(2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl) phenyl)arsonic acid
  参考文献：
  名称：

  2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile as novel inhibitor of receptor tyrosine kinase and PI3K/AKT/mTOR signaling pathway in glioblastoma

  摘要：

  Nerve growth factor receptor (NGFR), a member of kinase protein, is emerging as an important target for Glioblastoma (GBM) treatment. Overexpression of NGFR is observed in many metastatic cancers including GBM, promoting tumor migration and invasion. Hydrazones have been reported to effectively interact with receptor tyrosine kinases (RTKs). We report herein the synthesis of 23 arylhydrazones of active methylene compounds (AHAMCs) compounds and their anti-proliferative activity against GBM cell lines, LN229 and U87. Compound 8234, 2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile, was identified as the most active anti-neoplastic compound, with the IC50 value ranging 87 mu M - 107 mu M Molecular docking simulations of the synthesized compounds into the active site of tyrosine receptor kinase A (TrkA), demonstrated a strong binding affinity with 8234 and concurs well with the obtained biological results. 8234 was found to be a negative regulator of PI3K/Akt/mTOR pathway and an enhancer of p53 expression. In addition, 8234 treated GBM cells exhibited the downregulation of cyclins, cyclin-dependent kinases and other key molecules involved in cell cycle such as CCNE, E2F, CCND, CDK6, indicating that 8234 induces cell cycle arrest at G1/S. R234 also exerted its apoptotic effects independent of caspase3/7 activity, in both cell lines. In U87 cells, 8234 induced oxidative effects whereas LN229 cells annulled oxidative stress. The study thus concludes that 8234, being a negative modulator of RTKs and cell cycle inhibitor, may represent a novel class of anti-GBM drugs. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.01.021

文献信息

• New arylhydrazones of β-diketones and their optical and thermal properties
  作者：Zhen Ma、Abel M. Maharramov、Ismayil A. Aliyev、Irada N. Aliyeva、Maximilian N. Kopylovich、Gunel I. Amanullayeva、Kamran T. Mahmudov、Armando J.L. Pombeiro

  DOI：10.1016/j.molstruc.2012.03.054

  日期：2012.7

  New arylhydrazones of beta-diketones, 2-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl) benzoic acid (1) and (Z)-ethyl-2-(2-(2-nitrophenyl)hydrazono)-3-oxobutanoate (2), have been synthesized by reaction of activated beta-diketones with the corresponding aryldiazonium salts, and characterized by IR, H-1 and C-13 NMR spectroscopies and elemental analysis. In DMSO solution, 1 is stable exclusively in the hydrazone form, while 2 exists in DMSO and H2O solutions as a mixture of enol-azo and hydrazone tautomeric forms. In the latter case, an increase in the solvent polarity shifts the tautomeric balance to the enol-azo form. Solvatochromic, thermal and photoluminescent properties of 1,2 and the known related 2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)benzoic acid (3), (2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)phenyl)arsonic acid (4), (Z)-2-(2-(1,3-dioxo-1-phenylbutan-2-ylidene)hydrazinyl)benzoic acid (5) and 5-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl)-2,3-dihydrophthalazine-1,4-dione (6) were studied. The obtained UV-vis absorption spectra confirm that epsilon(max) depends on the solvent and on the nature of AHBD, but no clear correlation was found. Upon heating, 1-3,5 and 6 are stable up to 474 K and decompose in two steps whereas 4 decomposes in three steps starting from 343 K. The kinetic parameters of the thermal decomposition were estimated suggesting a low rate of the thermal decomposition. Compounds 2 and 3 exhibit luminescence with intense emission bands with maxima at lambda(em) of 466.0 (lambda(ex) = 318 nm) and 532.5 nm (lambda(ex) = 315 nm), respectively, while compounds 4 and 6 show low-intensity bands at lambda(em) of 501 (lambda(ex) = 396 nm) and 503 nm (lambda(ex) = 389 nm). Compounds 1 and 5 display no photoluminescence. (C) Crown Copyright 2012 Published by Elsevier B.V. All rights reserved.
• 2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile as novel inhibitor of receptor tyrosine kinase and PI3K/AKT/mTOR signaling pathway in glioblastoma
  作者：Anisha Viswanathan、Dinesh Kute、Aliyu Musa、Saravanan Konda Mani、Vili Sipilä、Frank Emmert-Streib、Fedor I. Zubkov、Atash V. Gurbanov、Olli Yli-Harja、Meenakshisundaram Kandhavelu

  DOI：10.1016/j.ejmech.2019.01.021

  日期：2019.3

  Nerve growth factor receptor (NGFR), a member of kinase protein, is emerging as an important target for Glioblastoma (GBM) treatment. Overexpression of NGFR is observed in many metastatic cancers including GBM, promoting tumor migration and invasion. Hydrazones have been reported to effectively interact with receptor tyrosine kinases (RTKs). We report herein the synthesis of 23 arylhydrazones of active methylene compounds (AHAMCs) compounds and their anti-proliferative activity against GBM cell lines, LN229 and U87. Compound 8234, 2-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzonitrile, was identified as the most active anti-neoplastic compound, with the IC50 value ranging 87 mu M - 107 mu M Molecular docking simulations of the synthesized compounds into the active site of tyrosine receptor kinase A (TrkA), demonstrated a strong binding affinity with 8234 and concurs well with the obtained biological results. 8234 was found to be a negative regulator of PI3K/Akt/mTOR pathway and an enhancer of p53 expression. In addition, 8234 treated GBM cells exhibited the downregulation of cyclins, cyclin-dependent kinases and other key molecules involved in cell cycle such as CCNE, E2F, CCND, CDK6, indicating that 8234 induces cell cycle arrest at G1/S. R234 also exerted its apoptotic effects independent of caspase3/7 activity, in both cell lines. In U87 cells, 8234 induced oxidative effects whereas LN229 cells annulled oxidative stress. The study thus concludes that 8234, being a negative modulator of RTKs and cell cycle inhibitor, may represent a novel class of anti-GBM drugs. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Complexes of copper(ii) with 3-(ortho-substituted phenylhydrazo)pentane-2,4-diones: syntheses, properties and catalytic activity for cyclohexane oxidation
  作者：Maximilian N. Kopylovich、Andreia C. C. Nunes、Kamran T. Mahmudov、Matti Haukka、Tatiana C. O. Mac Leod、Luísa M. D. R. S. Martins、Maxim L. Kuznetsov、Armando J. L. Pombeiro

  DOI：10.1039/c0dt01527j

  日期：——

  Reactions of copper(II) with 3-phenylhydrazopentane-2,4-diones X-2-C6H4–NHNCC(O)CH3}2 bearing a substituent in the ortho-position [X = OH (H2L1) 1, AsO3H2 (H3L2) 2, Cl (HL3) 3, SO3H (H2L4) 4, COOCH3 (HL5) 5, COOH (H2L6) 6, NO2 (HL7) 7 or H (HL8) 8] lead to a variety of complexes including the monomeric [CuL4(H2O)2]·H2O 10, [CuL4(H2O)2] 11 and [Cu(HL4)2(H2O)4] 12, the dimeric [Cu2(H2O)2(μ-HL2)2] 9

  铜（II）与3-苯基肼基戊烷-2,4-二酮X-2-C 6 H 4 –NHN C C（O）CH 3 } 2在邻位带有取代基的反应[X = OH（H 2 L 1）1，AsO 3 H 2（H 3 L 2）2，Cl（HL 3）3，SO 3 H（H 2 L 4）4，COOCH 3（HL 5）5，COOH（H2 L 6） 6，NO 2（HL 7） 7或H（HL 8） 8 ]导致各种络合物，包括单体[CuL 4（H 2 O） 2 ]·H 2 O 10，[CuL 4（ ħ 2 O） 2 ] 11和[铜（HL 4） 2（H 2 O） 4 ] 12，二聚物[Cu 2（H 2 O） 2（μ-HL 2）2 ] 9和聚合物[Cu（μ-L 6）] Ñ ] 13分的，常带有两个稠合的六元metallacycles。配合物10–12可以相互转化，具体取决于pH和温度，而Cu（ II）与4（在存在氰基胍 或者 咪唑（IM），得到单体化合物[铜（H