5448-47-5

Usage

Uses

Used in Pharmaceutical Industry:
INDOLE-3-ACETIC ACID HYDRAZIDE is used as a reactant for the preparation of various pharmaceutical agents due to its versatile chemical properties.
1. Antifungal Applications:
INDOLE-3-ACETIC ACID HYDRAZIDE is used as a reactant for the preparation of antifungal agents, which are essential in treating fungal infections.
2. Anticonvulsant Applications:
INDOLE-3-ACETIC ACID HYDRAZIDE is used as a reactant for the synthesis of anticonvulsant agents, which help in managing seizures and epilepsy.
3. Alpha-4 (α4) Integrin Antagonist Applications:
INDOLE-3-ACETIC ACID HYDRAZIDE is used as a reactant for the preparation of alpha-4 (α4) integrin antagonists, which have potential applications in treating various diseases, including autoimmune and inflammatory conditions.
4. Fluorescent Analogue Applications:
INDOLE-3-ACETIC ACID HYDRAZIDE is used as a reactant for the preparation of a fluorescent analogue of UDP-N-acetylglucosamine, which can be utilized in research and diagnostic applications.
5. Antioxidant Applications:
INDOLE-3-ACETIC ACID HYDRAZIDE is used as a reactant for the synthesis of antioxidant agents with myocardial protection properties, which can be beneficial in preventing heart damage and promoting heart health.
6. Antagonist Applications:
INDOLE-3-ACETIC ACID HYDRAZIDE is used as a reactant for the preparation of antagonist agents of neuropeptide Y receptors, which may have potential applications in treating obesity, anxiety, and other conditions related to neuropeptide Y signaling.
7. Antibacterial Applications:
INDOLE-3-ACETIC ACID HYDRAZIDE is used as a reactant for the synthesis of antibacterial agents, which are crucial in combating bacterial infections.
8. Monoamine Oxidase Inhibitor Applications:
INDOLE-3-ACETIC ACID HYDRAZIDE is used as a reactant for the preparation of potential monoamine oxidase inhibitors, which may have applications in treating depression and other mood disorders.

InChI:InChI=1/C10H11N3O/c11-13-10(14)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5,11H2,(H,13,14)

Upstream product

• 778-82-5 ethyl 3-indoleacetate 
• 87-51-4 indole-3-acetic acid 
• 120-72-9 indole 
• 1912-33-0 Indole-3-acetic acid methyl ester 

Downstream Products

• 82380-73-2 2-phenyl-5-<(3'-indolyl)methyl>-1,3,4-oxadiazole 
• 1191936-37-4 2-(1H-indol-3-yl)-N’-(4-methylbenzylidene)acetohydrazide 
• 293325-43-6 N’-(4-chlorobenzylidene)-2-(1H-indol-3-yl)acetohydrazide 
• 82380-74-3 2-((1H-indol-3-yl)methyl)-5-(4-nitrophenyl)-1,3,4-oxadiazole 
• 92487-26-8 (1H-Indol-3-yl)-acetic acid [1-(1-benzyl-1H-indol-3-yl)-meth-(Z)-ylidene]-hydrazide 
• 82380-75-4 2-((1H-indol-3-yl)methyl)-5-(4-chlorophenyl)-1,3,4-oxadiazole 
• 879-37-8 3-indolylacetamide 
• 1027901-28-5 C₃₈H₄₃N₇O₄ 
• 1025966-13-5 C₃₈H₄₃N₇O₃ 
• 925239-38-9 (R)-N-(1-(5-((1H-indol-3-yl)methyl)-4-(2,4-dimethoxybenzyl)-4H-1,2,4-triazol-3-yl)-2-(1H-indol-3-yl)ethyl)-2-amino-2-methylpropanamide 

Relevant academic research and scientific papers

Synthesis and screening of some novel substituted indoles contained 1,3,4-oxadiazole and 1,2,4-triazole moiety

A series of novel 3-[5-(1H-indol-3-yl-methyl)-2-oxo-[1,3,4]oxadiazol-3-yl] propionitrile (5), 3-[4-amino-3-(1H-indol-3-yl-methyl)-5-oxo-4,5-dihydro-[1,2,4] triazol-1-yl]propionitrile (6), 3-[5-(1H-indol-3-yl-methyl)-2-thioxo-[1,3,4] oxadiazol-3-yl]propionitrile (7) and 3-[4-amino-3-(1H-indol-3-yl-methyl)-5- thioxo-4,5-dihydro-[1,2,4]triazol-1-yl]propionitrile (8) were synthesized in good yields from the intermediate (1H-indol-3-yl)-acetic acid N′-(2-cyanoethyl)hydrazide (4). The chemical structures of the newly synthesized compounds were elucidated by their IR, 1H NMR and MS. Further, all the compounds were screened for their antimicrobial activity against Gram-positive, Gram-negative bacteria and also tested their ability toward anti-inflammatory activity.

A new CDK2 inhibitor with 3-hydrazonoindolin-2-one scaffold endowed with anti-breast cancer activity: Design, synthesis, biological evaluation, and in silico insights

Background: Cyclin-dependent kinases (CDKs) regulate mammalian cell cycle progression and RNA transcription. Based on the structural analysis of previously reported CDK2 inhibitors, a new compound with 3-hydrazonoindolin-2-one scaffold (HI 5) was well designed, synthesized, and biologically evaluated as a promising anti-breast cancer hit compound. Methods: The potential anti-cancerous effect of HI 5 was evaluated using cytotoxicity assay, flow cytometric analysis of apoptosis and cell cycle distribution, ELISA immunoassay, in vitro CDK2/cyclin A2 activity, and molecular operating environment (MOE) virtual docking studies. Results: The results revealed that HI 5 exhibits pronounced CDK2 inhibitory activity and cytotoxicity in human breast cancer MCF-7 cell line. The cytotoxicity of HI 5 was found to be intrinsically mediated apoptosis, which in turn, is associated with low Bcl-2 expression and high activation of caspase 3 and p53. Besides, HI 5 blocked the proliferation of the MCF-7 cell line and arrested the cell cycle at the G2/M phase. The docking studies did not confirm which one of geometric isomers (syn and anti) is responsible for binding affinity and intrinsic activity of HI 5. However, the molecular dynamic studies have confirmed that the syn-isomer has more favorable binding interaction and thus is responsible for CDK2 inhibitory activity. Discussion: These findings displayed a substantial basis of synthesizing further derivatives based on the 3-hydrazonoindolin-2-one scaffold for favorable targeting of breast cancer.

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.].

Synthesis, Pharmacological Evaluation and Molecular Docking Studies of N-[2-(1H-indol-3-yl)Acetyl]Arylsulfonohydrazides

Synthesis of heterocyclic compounds encompassing multiple functionalities and their biological screening is the most adapted strategy in the world for pharmacological evaluation of future drug candidates. The undertaken research was initiated by esterification 2-(1H-indol-3-yl)acetic acid (1) with catalytic amount of sulfuric acid in ethanol to ethyl 2-(1H-indol-3-yl)acetate (2), which was then reacted with hydrazine hydrate in methanol to achieve 2-(1H-indol-3-yl)acetohydrazide (3). The corresponding hydrazide 3 was reacted with a variety of arylsulfonyl chlorides (4a-j) in sodium carbonate solution (pH 9-10) to afford N-[2-(1H-indol-3-yl)acetyl]arylsulfonohydrazides (5a-j). The structural characterization of synthesized compounds was done by 1H-NMR, 13C-NMR, IR and EI-MS spectral data. Moreover, these derivatives were evaluated for anti-bacterial potentials along with their % age hemolytic and enzyme inhibitory activities. It was found that compounds 5a, 5b, 5d and 5h revealed good anti-bacterial against all the bacterial strains used in this study, while 5d, 5g and 5h exhibited good enzyme inhibition potentials against BChE which were close to the reference standard eserine. These compounds also revealed low values of % hemolytic activity. Results of computational docking were also found in agreement with the enzyme inhibition data.

Investigation of indole functionalized pyrazoles and oxadiazoles as anti-inflammatory agents: Synthesis, in-vivo, in-vitro and in-silico analysis

There are several potential side and adverse effects are found to be associated with the anti-inflammatory drugs in clinical practice. The long-term use of these clinical agents highly unsafe. It encouraged the development of novel heterocyclic compounds with potential anti-inflammatory activity and low to no toxicity. In present investigation, a total of 12 indole functionalized pyrazole and oxadiazole derivatives were designed, synthesized and evaluated for the in-vivo anti-inflammatory and analgesic potential. These compounds displayed comparable anti-inflammatory and analgesic potential to the reference drugs. Finally, molecular docking analysis was performed considering different anti-inflammatory targets to determine the mechanistic target of the designed molecules. Detailed analysis suggested that the molecules inhibit COX-2, preferably over other anti-inflammatory targets. The results suggested that two compounds (15c and 15f) were found promising candidates for the development of novel anti-inflammatory agents.

Synthesis of 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones and their protective activity against oxidative stress

A small library of 2-[(1H-indol-3-yl)methyl]-5-(alkylthio)-1,3,4-oxadiazoles was prepared, starting from indole-3-acetic acid methyl ester and its 5-methyl-substituted derivative. The synthetic route involved the formation of intermediate hydrazides, their condensation with carbon disulfide, and intramolecular cyclization to corresponding 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones. The latter were then S-alkylated, and in case of ester derivatives, they were further hydrolyzed into corresponding carboxylic acids. All 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones and their S-alkylated derivatives were then screened for their protective effects in vitro and in vivo. Methyl substitution on the indole ring and propyl, butyl, or benzyl substitution on sulfhydryl group-possessing compounds were revealed to protect Friedreich's ataxia fibroblasts against the effects of glutathione depletion induced by the γ-glutamylcysteine synthetase inhibitor, buthionine sulfoximine. Two of the active compounds also reproducibly increased the survival of Caenorhabditis elegans exposed to juglone-induced oxidative stress.

Synthesis of new urease enzyme inhibitors as antiulcer drug and computational study

In search of potent urease inhibitor indole analogues (1–22) were synthesized and evaluated for their urease inhibitory potential. All analogues (1–22) showed a variable degree of inhibitory interaction potential having IC50 value ranging between 0.60 ± 0.05 to 30.90 ± 0.90 μM when compared with standard thiourea having IC50 value 21.86 ± 0.90 μM. Among the synthesized analogues, the compounds 1, 2, 3, 5, 6, 8, 12, 14, 18, 20 and 22 having IC50 value 3.10 ± 0.10, 1.20 ± 0.10, 4.60 ± 0.10, 0.60 ± 0.05, 5.30 ± 0.20, 2.50 ± 0.10, 7.50 ± 0.20, 3.90 ± 0.10, 3.90 ± 0.10, 2.30 ± 0.05 and 0.90 ± 0.05 μM respectively were found many fold better than the standard thiourea. All other analogues showed better urease interaction inhibition. Structure activity relationship (SAR) has been established for all analogues containing different substituents on the phenyl ring. To understand the binding interaction of most active analogues with enzyme active site docking study were performed. Communicated by Ramaswamy H. Sarma.

Marine-inspired bis-indoles possessing antiproliferative activity against breast cancer; design, synthesis, and biological evaluation

Diverse indoles and bis-indoles extracted from marine sources have been identified as promising anticancer leads. Herein, we designed and synthesized novel bis-indole series 7a-f and 9a-h as Topsentin and Nortopsentin analogs. Our design is based on replacing the heterocyclic spacer in the natural leads by a more flexible hydrazide linker while sparing the two peripheral indole rings. All the synthesized bis-indoles were examined for their antiproliferative action against human breast cancer (MCF-7 and MDA-MB-231) cell lines. The most potent congeners 7e and 9a against MCF-7 cells (IC50 = 0.44 ± 0.01 and 1.28 ± 0.04 μM, respectively) induced apoptosis in MCF-7 cells (23.7-, and 16.8-fold increase in the total apoptosis percentage) as evident by the externalization of plasma membrane phosphatidylserine detected by Annexin V-FITC/PI assay. This evidence was supported by the Bax/Bcl-2 ratio augmentation (18.65- and 11.1-fold compared to control) with a concomitant increase in the level of caspase-3 (11.7- and 9.5-fold) and p53 (15.4- and 11.75-fold). Both compounds arrested the cell cycle mainly in the G2/M phase. Furthermore, 7e and 9a displayed good selectivity toward tumor cells (S.I. = 38.7 and 18.3), upon testing of their cytotoxicity toward non-tumorigenic breast MCF-10A cells. Finally, compounds 7a, 7b, 7d, 7e, and 9a were examined for their plausible CDK2 inhibitory action. The obtained results (% inhibition range: 16%-58%) unveiled incompetence of the target bis-indoles to inhibit CDK2 significantly. Collectively, these results suggested that herein reported bis-indoles are good lead compounds for further optimization and development as potential efficient anti-breast cancer drugs.

A double-indole hydrazone compound and use thereof

The invention provides a bisindole acylhydrazone compound shown as the formula I or salt, hydrate or crystals, accepted in the pharmacy, of the bisindole acylhydrazone compound. According to the bisindole acylhydrazone compound, R does not exist or is selected from alkylene of C1-5. The bisindole acylhydrazone compound has a certain antibacterial activity, and can serve as potential antibiotics or a daily chemical product. What is beyond the expectation is that compounds 4e-4h and compounds 4a-4c are quite similar in structure, the antibacterial activity of the compounds 4e-4h and the antibacterial activity of the compounds 4a-4c are obviously better than that of other compounds, particularly, the activity of the compound 4h is best and is remarkably better than that of compounds 4e-4g. The formula I is shown in the specification.

Indole hydrazone compounds

The invention provides a compound of the formula I as shown in the description. In the formula, R is connected with the carbon atom at the 2nd or 3rd site of indolyl and is selected from none or C1-3 alkylene. Molecular tweezers of bisindole acylhydrazone have a good recognition cooperation function on inspected malic acid, tartaric acid, ascorbic acid and tryptophan, and have no recognition cooperation function on other inspected organic acids such as lactic acid, oxalic acid, tyrosine, histidine and serine. Therefore, due to the selective recognition property of a molecular tweezers receptor has the potential to be applied to fields such as analysis and separation of relevant organic acids in biological medicines, and transportation of organic acid medicines.