A New Synthetic Method for the 2H‐[1,2,3]Thiadiazolo[5,4‐b]indoles.

Kondratieva, Maria L.; Pepeleva, Anna V.; Belskaia, Natalia P.; Koksharov, A. V.; Groundwater, P. V.; Robeyns, Koen; Meervelt, Luc Van; Dehaen, Wim; Fan, Zhijin; Бакулев, В. А.

doi:10.1002/chin.200731108

Cited by 2 publications

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“…Thiazolylhydrazones 13 – 18 were synthesized through the Hantzsch reaction [ 25 ] of bromomethyl ketones with 2-(5-methoxy-2-oxoindolin-3-ylidene)hydrazinecarbothioamide 12 [ 26 ] ( Scheme 2 ).…”

Section: Resultsmentioning

confidence: 99%

Insights into Structure-Activity Relationships of 3-Arylhydrazonoindolin-2-One Derivatives for Their Multitarget Activity on β-Amyloid Aggregation and Neurotoxicity

et al. 2018

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Despite the controversial outcomes of clinical trials executed so far, the prevention of β-amyloid (Aβ) deposition and neurotoxicity by small molecule inhibitors of Aβ aggregation remains a target intensively pursued in the search of effective drugs for treating Alzheimer’s disease (AD) and related neurodegeneration syndromes. As a continuation of previous studies, a series of new 3-(2-arylhydrazono)indolin-2-one derivatives was synthesized and assayed, investigating the effects of substitutions on both the indole core and arylhydrazone moiety. Compared with the reference compound 1, we disclosed equipotent derivatives bearing alkyl substituents at the indole nitrogen, and fairly tolerated bioisosteric replacements at the arylhydrazone moiety. For most of the investigated compounds, the inhibition of Aβ40 aggregation (expressed as pIC50) was found to be correlated with lipophilicity, as assessed by a reversed-phase HPLC method, through a bilinear relationship. The N1-cyclopropyl derivative 28 was tested in cell-based assays of Aβ42 oligomer toxicity and oxidative stress induced by hydrogen peroxide, showing significant cytoprotective effects. This study confirmed the versatility of isatin in preparing multitarget small molecules affecting different biochemical pathways involved in AD.

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Section: Resultsmentioning

confidence: 99%

Insights into Structure-Activity Relationships of 3-Arylhydrazonoindolin-2-One Derivatives for Their Multitarget Activity on β-Amyloid Aggregation and Neurotoxicity

et al. 2018

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“…1,2,3-Thiadiazoles can be synthesized via different methods , . The key intermediate, 4-methyl-1,2,3-thiadiazole carboxylic acid in our study, was prepared by the Hurd−Mori reaction with good yield (Scheme ).…”

Section: Resultsmentioning

confidence: 98%

Synthesis and Biological Activity Evaluation of 1,2,3-Thiadiazole Derivatives as Potential Elicitors with Highly Systemic Acquired Resistance

Fan

Shi

Zhang

et al. 2009

J. Agric. Food Chem.

108

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Elicitors provide a broad spectrum of systemic acquired resistance by altering the physical and physiological status of the host plants and, therefore, are among the most successful directions in modern pesticide development for plant protection. To develop a novel elicitor with highly systemic acquired resistance, two series of thiazole- and oxadiazole-containing thiadiazole derivatives were rationally designed and synthesized according to the principle of combination of bioactive substructures in this work. Their structures were characterized by (1)H nuclear magnetic resonance (NMR), infrared (IR), high-resolution mass spectrometry (HRMS), or elemental analysis. Their potential systemic acquired resistance as an elicitor was also evaluated; bioassay results indicated that, among the 23 compounds synthesized, three compounds, 10a, 10d, and 12b, displayed better systemic acquired resistance than the positive control, tiadinil, a commercialized 1,2,3-thiadiazole-based elicitor. In addition, three other compounds, 10f, 12c, and 12j, exhibited a certain degree of fungus growth inhibition in vitro or in vivo. Our results demonstrated that, in combination of bioactive substructures is an interesting exploration for novel pesticide development, thiazole- and oxadiazole-containing thiadiazole derivatives are potential elicitors with good systemic acquired resistance.

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A New Synthetic Method for the 2H‐[1,2,3]Thiadiazolo[5,4‐b]indoles.

Cited by 2 publications

References 1 publication

Insights into Structure-Activity Relationships of 3-Arylhydrazonoindolin-2-One Derivatives for Their Multitarget Activity on β-Amyloid Aggregation and Neurotoxicity

Insights into Structure-Activity Relationships of 3-Arylhydrazonoindolin-2-One Derivatives for Their Multitarget Activity on β-Amyloid Aggregation and Neurotoxicity

Synthesis and Biological Activity Evaluation of 1,2,3-Thiadiazole Derivatives as Potential Elicitors with Highly Systemic Acquired Resistance

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