5448-47-5

Basic information

• Product Name: INDOLE-3-ACETIC ACID HYDRAZIDE
• Synonyms: 1-(3-indolylacetyl)-hydrazin;1-(3-Indolylacetyl)hydrazine;1H-Indole-3-acetic acid, hydrazide;2-(1H-Indol-3-yl)acetohydrazide;3-Indolylacetic acid hydrazide;Hydrazine, 1-(3-indolylacetyl)-;INDOLE 3-ACETHYDRAZIDE;INDOLE-3-ACETIC ACID HYDRAZIDE
• CAS NO: 5448-47-5
• Molecular Formula: C₁₀H₁₁N₃O
• Molecular Weight: 189.21
• EINECS: 226-672-7
• Product Categories: Pyrroles & Indoles;Building Blocks;Heterocyclic Building Blocks;Indoles;Building Blocks;C10;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 5448-47-5.mol
• Article Data: 24

Chemical Properties

• Melting Point: 142-145 °C(lit.)
• Boiling Point: 324.47°C (rough estimate)
• Flash Point: 267.1 °C
• Appearance: beige to pale brown fine crystalline powder
• Density: 1.1654 (rough estimate)
• Vapor Pressure: 7.76E-11mmHg at 25°C
• Refractive Index: 1.4830 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 13.23±0.18(Predicted)
• CAS DataBase Reference: INDOLE-3-ACETIC ACID HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: INDOLE-3-ACETIC ACID HYDRAZIDE(5448-47-5)
• EPA Substance Registry System: INDOLE-3-ACETIC ACID HYDRAZIDE(5448-47-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 24/25-26
• WGK Germany: 3
• RTECS: NL3600000
• HazardClass: IRRITANT
• Hazardous Substances Data: 5448-47-5(Hazardous Substances Data)

Usage

Chemical Properties

beige to pale brown fine crystalline powder

Uses

Different sources of media describe the Uses of 5448-47-5 differently. You can refer to the following data:
1. Reactant for preparation of:? ;Antifungal agents1? ;Anticonvulsant agents2? ;Alpha-4 (α4) integrin antagonists3? ;A fluorescent analogue of UDP-N-acetylglucosamine4? ;Antioxidant agents with myocardial protection properties5? ;Antagonist agents of neuropeptide Y receptors6? ;Antibacterial agents7? ;Potential monoamine oxidase inhibitors8
2. Reactant for preparation of:Antifungal agentsAnticonvulsant agentsAlpha-4 (α4) integrin antagonistsA fluorescent analogue of UDP-N-acetylglucosamineAntioxidant agents with myocardial protection propertiesAntagonist agents of neuropeptide Y receptorsAntibacterial agentsPotential monoamine oxidase inhibitors

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

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

Downstream Products

• 15316-22-0 (E)-N'-benzylidene-2-(1H-indol-3-yl)acetohydrazide 
• 13113-08-1 2-(2-(1H-indol-3-yl)acetamido)acetic acid 
• 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 
• 153595-90-5 2-(2-(1H-indol-3-yl)acetyl)-N-phenylhydrazincarbothioamide 
• 879-37-8 3-indolylacetamide 
• 209670-81-5 3-[(5-nitrothiazol-2-yl)mercapto]-4-phenyl-5-(pyrid-2-yl)-1,2,4-triazole 
• 15316-22-0 N'-benzylidene-2-(1H-indole-3-yl)acetohydrazide 
• 413617-68-2 N'-(4-methoxybenzylidene)-2-(1H-indole-3-yl)acetohydrazide 
• 15316-27-5 N'-(1-phenylethylidene)-2-(1H-indole-3-yl)acetohydrazide 

Relevant articles and documents

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.

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.].

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.