2-[(2-hydroxybenzoyl)hydrazonomethyl]-1H-pyrrole | 19015-16-8

• 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-hydroxybenzoyl)hydrazonomethyl]-1H-pyrrole
• 英文别名: Benzoic acid, 2-hydroxy-, (1H-pyrrol-2-ylmethylene)hydrazide；2-hydroxy-N-[(E)-1H-pyrrol-2-ylmethylideneamino]benzamide
• CAS: 19015-16-8
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: SSFAKFBVXKBZAY-RIYZIHGNSA-N

物化性质

• 熔点：
  222-223 °C (decomp)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(2-hydroxybenzoyl)hydrazonomethyl]-1H-pyrrole 、 邻硝基苯甲醛 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以59%的产率得到1,9-bis[(2-hydroxybenzoyl)hydrazonomethyl]-5-(2-nitrophenyl)dipyrromethane
  参考文献：
  名称：

  Spectroscopic, reactivity and NLO analysis of new hydrazone-containing dipyrromethane using experimental and theoretical approaches

  摘要：

  The molecular structure and detailed spectroscopic analysis of a novel synthesized dipyrromethane: 1,9-bis[(2-hydroxybenzoyl)-hydrazonomethyl]-5-(2-nitrophenyl)-dipyrromethane (3) have been performed using both experimental techniques and theoretical calculations. Thermodynamic parameters (H, G, S) of reactants and products have been used to investigate the nature of synthesis. The singlet chemical shift at 5.343 ppm of meso-proton designates formation of product molecule (3). TD-DFT has been used to calculate oscillatory strength U) and wavelength absorption maxima (lambda(max)) of various electronic excitations and their nature within molecule. The molecular orbital coefficients and molecular plots analysis assign nature of electronic excitations as pi ->pi*. Natural bond orbital (NBO) analysis has been carried out to investigate the intramolecular H-bonding, conjugative and hyperconjugative interactions within molecule. The result of intramolecular hydrogen bonding (O68-H69...O22/O66-H67...O45) is obvious in H-1 NMR, FT-IR and NBO due to down field chemical shift, vibrational red shift, and n(2)(O22) -> sigma*(O68-H69)/n(2)(O45) -> sigma*(O66-H67) interactions energies 105.12/104.91 (kJ/mot), respectively. To investigate the strength and nature of H-bonding, topological parameters at bond critical points (BCP) have been analyzed by 'Quantum theory of Atoms in molecules' (QTAIM). Local reactivity descriptors- Fukui functions(f(k)(+),f(k)(-)), local softnesses (s(k)(+),S-k(-)) and electrophilicity indices (omega(+)(k),omega(-)(k)) analyses have been performed to find out the reactive sites of the molecule. The computed first hyperpolarizability (beta(0) = 14.30 x 10(-30) esu) evaluates the molecule to be suitable for non-linear optical (NLO) response. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.03.007
• 作为产物：
  描述：

  2-吡咯甲醛 、 水杨酰肼 以 甲醇 为溶剂， 生成 2-[(2-hydroxybenzoyl)hydrazonomethyl]-1H-pyrrole
  参考文献：
  名称：

  Spectroscopic, reactivity and NLO analysis of new hydrazone-containing dipyrromethane using experimental and theoretical approaches

  摘要：

  The molecular structure and detailed spectroscopic analysis of a novel synthesized dipyrromethane: 1,9-bis[(2-hydroxybenzoyl)-hydrazonomethyl]-5-(2-nitrophenyl)-dipyrromethane (3) have been performed using both experimental techniques and theoretical calculations. Thermodynamic parameters (H, G, S) of reactants and products have been used to investigate the nature of synthesis. The singlet chemical shift at 5.343 ppm of meso-proton designates formation of product molecule (3). TD-DFT has been used to calculate oscillatory strength U) and wavelength absorption maxima (lambda(max)) of various electronic excitations and their nature within molecule. The molecular orbital coefficients and molecular plots analysis assign nature of electronic excitations as pi ->pi*. Natural bond orbital (NBO) analysis has been carried out to investigate the intramolecular H-bonding, conjugative and hyperconjugative interactions within molecule. The result of intramolecular hydrogen bonding (O68-H69...O22/O66-H67...O45) is obvious in H-1 NMR, FT-IR and NBO due to down field chemical shift, vibrational red shift, and n(2)(O22) -> sigma*(O68-H69)/n(2)(O45) -> sigma*(O66-H67) interactions energies 105.12/104.91 (kJ/mot), respectively. To investigate the strength and nature of H-bonding, topological parameters at bond critical points (BCP) have been analyzed by 'Quantum theory of Atoms in molecules' (QTAIM). Local reactivity descriptors- Fukui functions(f(k)(+),f(k)(-)), local softnesses (s(k)(+),S-k(-)) and electrophilicity indices (omega(+)(k),omega(-)(k)) analyses have been performed to find out the reactive sites of the molecule. The computed first hyperpolarizability (beta(0) = 14.30 x 10(-30) esu) evaluates the molecule to be suitable for non-linear optical (NLO) response. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.03.007

文献信息

• SMALL MOLECULE INHIBITORS OF HIV-1 ENTRY AND METHODS OF USE THEREOF
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US20170298056A1

  公开（公告）日：2017-10-19

  Described herein are small-molecule compounds that specifically inhibit a wide range of HIV-1 isolates without interfering with CD4 or CCR5 binding. Methods of using die compounds for treating or preventing HIV infection are also described.
• METHOD OF MODULATING RIBONUCLEOTIDE REDUCTASE
  申请人：CASE WESTERN RESERVE UNIVERSITY

  公开号：US20210299095A1

  公开（公告）日：2021-09-30

  A method of modulating ribonucleotide reductase activity in a neoplastic cell includes administering to the cell an amount of a hydrazone or hydrazine ribonucleotide reductase modulator (RRmod), the amount being effective to inhibit neoplastic cell growth.
• [EN] COMPOSITIONS AND METHODS BASED ON HIV GP120 MUTANTS<br/>[FR] COMPOSITIONS ET PROCÉDÉS FONDÉS SUR DES MUTANTS GP120 DU VIH
  申请人：CENTRE HOSPITALIER DE LUNIVERSITE DE MONTREAL

  公开号：WO2021056105A1

  公开（公告）日：2021-04-01

  Compositions and methods based on the use of mutated HIV-1 gp120 polypeptides having amino acid substitutions at positions 61, 105, 108, 375, 474, 475 and 476 are described. These mutated HIV-1 gp120 polypeptides, which make the HIV env protein more amenable to adopt specific conformations when contacted with gp120 ligands, may be useful as vaccines or tools to identify and characterize agents modulating HIV infection.