Synthesis and Structure−Activity Relationships of 2-Amino-1-aroylnaphthalene and 2-Hydroxy-1-aroylnaphthalenes as Potent Antitubulin Agents

Reddy, G. Randheer; Kuo, Ching‐Chuan; Tan, Uan-Kang; Coumar, Mohane Selvaraj; Chang, Chen; Chiang, Yi-Kun; Lai, Mei-Jung; Yeh, Jan-Ying; Wu, Su-Ying; Chang, Jang‐Yang; Liou, Jing Ping; Hsieh, Hsing‐Pang

doi:10.1021/jm8008635

Cited by 29 publications

(12 citation statements)

References 34 publications

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“…2,6-Dihydroxynaphthalene was initially methylated using NaH and iodomethane to afford 2,6dimethoxynaphthalene, 32 which was subsequently formylated with N-methylformanilide and POCl 3 . 33 Selective deprotection of the o-methoxy group of 2,6-dimethoxy-1-naphthalenecarbaldehyde was achieved by treating it with MgBr 2 and NaI in CH 3 CN at 150 °C. Nitration of 2-hydroxy-1-naphthaldehyde with concentrated nitric acid afforded the required 2-hydroxy-6nitro-1-naphthaldehyde 10.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines

et al. 2016

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Spiropyrans and spirooxazines represent an important class of photochromic compounds with a wide variety of applications. In order to effectively utilize and design these photoswitches it is desirable to understand how the substituents affect photochromic properties, and how the different structural motifs compare under identical conditions. In this work a small library of photoswitches was synthesized in order to comparatively evaluate the effect of substituent modifications and structure on photochromism. The library was designed to modify positions that were believed to have the greatest effect on C-O bond lability and therefore the photochromic properties. Herein we report a comparative analysis of the UV and visible light responses of 30 spiropyrans, spiroindolinonaphthopyrans, and spirooxazines. The influence of gadolinium(III) binding was also investigated on the library of compounds to determine its effect on photoswitching. Both assays demonstrated different trends in substituent and structural requirements for optimal photochromism.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines

et al. 2016

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“…Benzohydrazide is another scaffold that has been reported for its wide range of activities, including anticonvulsant antitumor, antioxidant, antileishmanial antifungal and antibacterial properties (Figure1 : 2 ) . The antibacterial property of benzohydrazides was supported by some shreds of evidence in which Vijayaraj et al., 2007 reported the activity of benzohydrazide derivatives against pathogens like E. coli , S. aureus , K. pneumonia , P. aeruginosa using disc diffusion method (Figure : 3 ) .…”

Section: Introductionmentioning

confidence: 56%

Synthesis and Evaluation of Aryl/Heteroaryl Benzohydrazide and Phenylacetamide Derivatives as Broad‐Spectrum Antibacterial Agents

2020

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A series of novel aryl/heteroaryl benzohydrazide (3 a–d) and aryl/heteroaryl phenylacetamide derivatives (5 a–g) were designed, synthesized and characterized by spectral techniques. The synthesized compounds were screened against pathogenic bacteria to assess their in vitro antibacterial properties. From the eleven synthesized compounds, 3 b(0.7 μg/mL) and 3 c(0.6 μg/mL) exhibited potent activity against a panel of organisms especially against S. aureus. Further, time‐kill study confirmed the bactericidal activity of 3 b and 3 c against S. aureus, that may be because of conjoined benzothiazole and benzohydrazide moieties in their structures. Extra‐precision docking and binding free energy calculation were also performed for the title compounds, in which 3 c(‐6.23 kcal/mol) exhibited higher binding affinity against S. aureus ParE (SaParE). Molecular dynamic simulation of 50 ns was used to find out the stability of predicted binding conformation of 3 c/SaParE. Besides, assessment of in silico ADMET properties illustrates that the title compounds were in agreement with Lipinski's rule parameters. The study could offer a unique framework that may lead to the discovery of novel antibacterials.

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“…Molecular scaffolds such as 2‐hydroxybenzophenones present in natural products, are associated with immense biological properties, Some of these skeletons are shown in Figure , of which hydroxyphenstatin ( 1 ) exhibits potent cytotoxicity and inhibits tubulin polymerization. [4b] Similarly, 1,5‐dimethoxyajacareubin ( 2 ) extracted from the stem bark of Garcinia buchananii has strong antioxidative, oxygen‐radical absorbance capacity.…”

Section: Introductionmentioning

confidence: 99%

Rhodium‐Catalyzed Directing‐Group‐Assisted Aldehydic C–H Arylations with Aryl Halides

Rao

Ramakrishna

2017

Eur J Org Chem

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A rhodium‐catalyzed general protocol for the directing‐group‐assisted arylation of aromatic aldehydic C–H bonds was developed. This method involves either hydroxy‐ or amino‐group‐directed aldehyde C–H arylation with various aryl halides. A broad synthetic scope for the preparation of 2‐hydroxybenzophenones was established with electronically variant salicylaldehydes and aryl halides with chemo‐ and regioselective possibilities. The developed protocol was also applied in the synthesis of medicinally important 3‐salicyloylpyridines in high yields.

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Synthesis and Structure−Activity Relationships of 2-Amino-1-aroylnaphthalene and 2-Hydroxy-1-aroylnaphthalenes as Potent Antitubulin Agents

Cited by 29 publications

References 34 publications

Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines

Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines

Synthesis and Evaluation of Aryl/Heteroaryl Benzohydrazide and Phenylacetamide Derivatives as Broad‐Spectrum Antibacterial Agents

Rhodium‐Catalyzed Directing‐Group‐Assisted Aldehydic C–H Arylations with Aryl Halides

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