15317-58-5

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-3-carboxylic acid hydrazide is used as a building block for the synthesis of various pharmaceutical compounds, leveraging its unique chemical structure to create new drugs with potential therapeutic benefits.
Used in Medicinal Chemistry Research:
As a compound with demonstrated biological activities, 1H-Indole-3-carboxylic acid hydrazide is used as a subject of interest in drug discovery and development. Its anticancer properties are being explored for potential applications in treating various types of cancer.
Used in Antimicrobial Agents Development:
The antimicrobial properties of 1H-Indole-3-carboxylic acid hydrazide make it a candidate for the development of new antimicrobial agents, which could be crucial in combating drug-resistant infections.

InChI:InChI=1/C9H9N3O/c10-12-9(13)7-5-11-8-4-2-1-3-6(7)8/h1-5,11H,10H2,(H,12,13)

Upstream product

• 59496-25-2 Indole-3-carbonyl chloride 
• 776-41-0 indole-3-carboxylic acid ethyl ester 
• 942-24-5 3-methoxycarbonylindole 
• 30030-90-1 2,2,2-trichloro-1-(1H-indol-3-yl)ethan-1-one 
• 771-50-6 1H-indole-3-carboxylic acid 
• 1160437-52-4 1,1-dimethylethyl 2-(1H-indol-3-ylcarbonyl)hydrazinecarboxylate 
• 120-72-9 indole 
• 487-89-8 Indole-3-carboxaldehyde 

Downstream Products

• 54584-06-4 2-(1H-indol-3-yl)-5-phenyl-1,3,4-oxadiazole 
• 82380-66-3 2-(para-nitrophenyl)-5-(3'-indolyl)-1,3,4-oxadiazole 
• 82380-78-7 N¹-benzoyl-N²-(3-indolyl)hydrazine 
• 94830-19-0 2-(1H-indole-3-carbonyl)-N-phenylhydrazinecarbothioamide 
• 82380-67-4 3-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-indole 
• 82380-79-8 N¹-(4-nitrobenzoyl)-N²-(3-indolyl)hydrazine 
• 94829-95-5 3-(indol-3-yl)-4-phenyl-1,2,4-triazole 
• 94830-21-4 5-(indol-3-yl)-4-phenyl-1,2,4-triazoline-3-thione 
• 94829-93-3 5-(1H-indol-3-yl)-N-phenyl-1,3,4-oxadiazol-2-amine 
• 94830-22-5 5-(indol-3-yl)-2-phenylamino-1,3,4-thiadiazole 
• 94829-97-7 1-(indol-3-ylcarbonyl)-4-phenyl-S-methylisothiosemicarbazide 
• 1431138-09-8 C₂₅H₁₇ClN₄O 
• 1431138-10-1 C₂₆H₂₀N₄O₂ 
• 1431138-11-2 C₂₅H₁₆BrClN₄O 

Relevant academic research and scientific papers

Microwave irradiation synthesis of novel indole triazole Schiff base fluorescent probe for Al3+ ion

An efficient triazole Schiff base fluorescent Al3+-probe 4-((2-hydroxybenzylidene) amino)-5-(1H-indol-3-yl)-4H-1,2,4-triazole-3-thiol (H2L) was designed and synthesized under microwave irradiation. The structure of fluorescent probe H2L was characterized by spectral data and elemental analysis. The probe H2L displays excellent chemo-selectivity towards Al3+ over other metal ions, which can directly inspect with the naked eye under UV lamp. The limit of detection of the probe H2L for Al3+ could reach 29.9 nM. The binding stoichiometry between H2L and Al3+ was determined from the Job's plot to be 1:1, the association constant (Ka) of 9.31 × 104 M?1, and further verified with fluorescence titration, ESI-MS and 1H NMR study.

Synthesis and functionalization of the 3-(1, 3, 4-oxadiazol-2-yl)-1H- indoles

A modified method is proposed for the preparative synthesis of 3-(1, 3, 4-oxadiazol-2-yl)-1H-indoles in high yield. We are the first to demonstrate the functionalization of this heterocyclic system by alkylation. In particular, syntheses are reported for [3-(1, 3, 4-oxadiazol-2-yl)-1H-indol-1-yl]acetic acids and their amide derivatives.

Development of 2-oindolin-3-ylidene-indole-3-carbohydrazide derivatives as novel apoptotic and anti-proliferative agents towards colorectal cancer cells

Mitochondrial anti-apoptotic Bcl2 and BclxL proteins, are overexpressed in multiple tumour types, and has been involved in the progression and survival of malignant cells. Therefore, inhibition of such proteins has become a validated and attractive target for anticancer drug discovery. In this manner, the present studies developed a series of novel isatin–indole conjugates (7a-j and 9a-e) as potential anticancer Bcl2 and BclxL inhibitors. The progression of the two examined colorectal cancer cell lines was significantly inhibited by all of the prepared compounds with IC50 ranges132–611 nM compared to IC50 = 4.6 μM for 5FU, against HT-29 and IC50 ranges 37–468 nM compared to IC50 = 1.5 μM for 5FU, against SW-620. Thereafter, compounds 7c and 7g were selected for further investigations. Interestingly, both compounds exhibited selective cytotoxicity against both cell lines with high safety to normal fibroblast (HFF-1). In addition, both compounds 7c and 7g induced apoptosis and inhibited Bcl2 and BclxL expression in a dose-dependent manner. Collectively, the high potency and selective cytotoxicity suggested that conjugates 7c and 7g could be a starting point for further optimisation to develop novel pro-apoptotic and antitumor agents towards colon cancer.

Synthesis and biological evaluation of novel 4,5-bisindolyl-1,2,4-Triazol-3- ones as glycogen synthase kinase-3β inhibitors and neuroprotective agents

A series of novel 4,5-bisindolyl-1,2,4-Triazol-3-ones were designed, prepared and evaluated for their glycogen synthase kinase (GSK)-3β inhibitory activities. Compounds exhibited favorable inhibitory potency towards GSK-3β kinase at the molecular level and in cells indicated by significantly reducing GSK-3β substrate Tau phosphorylation at Ser396 in primary neurons showing the inhibition of cellular GSK-3β. In an in vitro model of neuronal injury, compounds 6b, 6d and 6f prevented glutamate-induced neuronal death which was closely associated with cerebral ischemic stroke. Preliminary structure-Activity relationship was examined and showed that different substituents on the indole ring had significant influences on the GSK-3β inhibitory potency. These findings may provide new insights into the development of novel GSK-3β inhibitors as neuroprotective agents.

Design of balanced COX inhibitors based on anti-inflammatory and/or COX-2 inhibitory ascidian metabolites

The aim of this study was to design and synthesize COX-1/COX-2 balanced inhibitors incorporating the structural motifs of anti-inflammatory ascidian metabolites. We designed a series of substituted indole analogs that incorporate the key structures of the ascidian metabolites, herdmanines C and D. The synthesized analogs were tested for their inhibitory activity against COX-1 and COX-2, and compound 5m, which displayed balanced inhibition, was further evaluated for in vitro anti-inflammatory activity. Compound 5m suppressed the expression of pro-inflammatory factors, including iNOS, COX-2, TNF-α, and IL-6 in LPS-stimulated murine RAW264.7 macrophages. The reduction of PGE2, NO, and ROS was also observed, together with the suppression of NF-κB, IKK, and IκBα phosphorylation. Our results characterized 5m as a COX-1/COX-2 balanced inhibitor that subsequently caused ROS inhibition and NF-κB suppression, and culminated in the suppression of iNOS, COX-2, TNF-α, and IL-6 expression.

Diversity-oriented synthesis and antifungal activities of novel pimprinine derivative bearing a 1,3,4-oxadiazole-5-thioether moiety

Abstract: Based on the strategy of diversity-oriented synthesis and the structures of natural product pimprinine and streptochlorin, two series of novel pimprinine derivatives containing 1,3,4-oxadiazole-5-thioether moieties were efficiently synthesized under the optimized reaction conditions. Biological assays conducted at Syngenta showed the designed derivatives displayed an altered pattern of biological activity, of which 5h was identified as the most promising compound with strong activity against Pythium dissimile and also a broad antifungal spectrum in primary screening. Further structural optimization of pimprinine and streptochlorin derivatives is well under way, aiming to discover synthetic analogues with improved antifungal activity. Graphic abstract: Two series of novel pimprinine derivatives containing 1,3,4-oxadiazole-5-thioether moieties wereefficiently synthesized through diversity-oriented synthesis strategy under the optimizedconditions. Biological assays showed the designed derivatives exhibited potential activity.[Figure not available: see fulltext.].

NOVEL INDOLE DERIVATIVES AND COMPOSITION FOR PREVENTING OR TREATING INFLAMMATORY DISEASES COMPRISING THE SAME

The present invention relates to a novel indole derivative and a composition for preventing or treating inflammatory diseases comprising the same. More specifically, since a series of substituted indole derivative compounds combining a core structure of an anti-inflammatory seaweed metabolite are designed and synthesized, and inhibitory activity and anti-inflammatory activity on COX-1 and COX-2 in the compound are confirmed, the compound can be used as an effective pharmaceutical composition or health functional food composition for preventing, alleviating or treating inflammatory diseases.

Indole derivatives containing disulfide alkyl heterocyclic structure or stereoisomer, salt or solvate of the indole derivatives

The invention relates to a preparation method and application of indole derivatives containing a disulfide alkyl heterocyclic structure. The compounds have a general structure as shown in a general formula (I) shown in the specification. Indole compounds

Design, Synthesis, and Pharmacological Evaluation of First-in-Class Multitarget N-Acylhydrazone Derivatives as Selective HDAC6/8 and PI3Kα Inhibitors

Targeting histone deacetylases (HDACs) and phosphatidylinositol 3-kinases (PI3Ks) is a very promising approach for cancer treatment. This manuscript describes the design, synthesis, in vitro pharmacological profile, and molecular modeling of a novel class of N-acylhydrazone (NAH) derivatives that act as HDAC6/8 and PI3Kα dual inhibitors. The surprising selectivity for PI3Kα may be related to differences in the conformation in the active site. Cellular studies showed that these compounds act in HDAC6 inhibition and the PI3/K/AKT/mTOR pathway. The compounds that are selective for inhibition of HDAC6/8 and inhibit PI3Kα show potential for the treatment of cancer.

Derivative containing 1, 2, 4-mercaptotriazole and preparation method and application of derivative

The invention relates to the technical field of medicinal chemistry, in particular to a derivative containing 1, 2, 4-mercaptotriazole and a preparation method and application of the derivative. The derivative containing 1, 2, 4-mercaptotriazole has relatively good inhibitory activity on DCN1-UBC12 protein-protein interaction, so that the 1, 2, 4-mercaptotriazole derivative has relatively good inhibitory activity on DCN1-UBC12 protein-protein interaction. According to the record of the embodiment, compared with NAcM-COV, the derivative containing 1, 2, 4-mercaptotriazole provided by the invention has better inhibitory activity on DCN1-UBC12 protein-protein interaction, and the structural formula of the derivative containing 1, 2, 4-mercaptotriazole is shown in the specification.