158144-17-3

Basic information

• Product Name: (1-METHYL-1H-PYRROL-2-YL)-ACETIC ACID HYDRAZIDE
• Synonyms: CHEMBRDG-BB 3001503;AKOS BBS-00004127;(1-METHYL-1H-PYRROL-2-YL)-ACETIC ACID HYDRAZIDE;2-(1-METHYL-1H-PYRROL-2-YL)ACETOHYDRAZIDE;2-(1-methyl-1H-pyrrol-2-yl)acetohydrazide(SALTDATA: FREE);2-(1-methyl-2-pyrrolyl)acetohydrazide;2-(1-methylpyrrol-2-yl)acetohydrazide;2-(1-methylpyrrol-2-yl)ethanehydrazide
• CAS NO: 158144-17-3
• Molecular Formula: C₇H₁₁N₃O
• Molecular Weight: 153.18
• Product Categories: Heterocyclic Building Blocks
• Mol File: 158144-17-3.mol

Chemical Properties

• Boiling Point: 390.8°C at 760 mmHg
• Flash Point: 190.2°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 2.58E-06mmHg at 25°C
• Refractive Index: 1.582
• PKA: 13.25±0.18(Predicted)
• CAS DataBase Reference: (1-METHYL-1H-PYRROL-2-YL)-ACETIC ACID HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (1-METHYL-1H-PYRROL-2-YL)-ACETIC ACID HYDRAZIDE(158144-17-3)
• EPA Substance Registry System: (1-METHYL-1H-PYRROL-2-YL)-ACETIC ACID HYDRAZIDE(158144-17-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 158144-17-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H11N3O/c1-10-4-2-3-6(10)5-7(11)9-8/h2-4H,5,8H2,1H3,(H,9,11)

Upstream product

• 21898-59-9 1-methylpyrrole-2-acetic acid 
• 49669-45-6 ethyl (1-methyl-1H-pyrrol-2-yl)acetate 

Downstream Products

• 351157-86-3 C₁₄H₁₆N₄O₂ 
• 716364-11-3 C₁₄H₂₂N₄O₂ 
• 891005-41-7 4-(4-bromophenyl)-1-[(1-methylpyrrol-2-yl)acetyl]semicarbazide 
• 1217115-24-6 4-benzyl-1-[(1-methylpyrrol-2-yl)acetyl]semicarbazide 
• 904850-40-4 C₁₆H₂₀N₄O₃ 
• 1130206-86-8 4,4'-bis[3-(1-methylpyrrol-2-yl)methyl-1,2,4-triazolin-5-on-4-yl]diphenylmethane 
• 1217115-30-4 4-bromophenyl-3-[(1-methylpyrrol-2-yl)methyl]-4,5-dihydro-1,2,4-triazolin-5-one 
• 875329-75-2 C₁₅H₁₈N₄O₂S 
• 875329-80-9 3-[(1-methylpyrrol-2yl)methyl]-4-(4-methoxyphenyl)-1,2,4-triazoline-5-thione 
• 503020-90-4 1-[(1-methylpyrrol-2-yl)acetyl]-4-phenylthiosemicarbazide 
• 682745-47-7 3-[(1-methylpyrrol-2yl)methyl]-4-phenyl-1,2,4-triazoline-5-thione 
• 875329-77-4 C₁₅H₁₈N₄OS 
• 875329-82-1 4-benzyl-3-[(1-methylpyrrol-2yl)methyl]-1,2,4-triazoline-5-thione 
• 869946-27-0 4-ethyl-3-[(1-methylpyrrol-2yl)methyl]-1,2,4-triazoline-5-thione 

Relevant articles and documents

Synthesis and structural study of some N-acyl-4-allylsemicarbazides and the product of their cyclization with a potential antimicrobial activity

In this paper semicarbazide (2a-2h) and 1,2,4-trazole (3a-3h) derivatives with allyl group were synthesized. All compounds were tested in vitro for their antimicrobial activity showing different activity to E. coli, S. aureus, S. epidermidis, M. smegmatis, M. phlei and M. tuberculosis H37Ra. The antimicrobial activity is showed 2g against S. epidermidis, 3g against E. coli and S. epidermidis and 3h against E. coli. The crystal structure of determinations of 2b, 2d, 3b, 3c and 3e were undertaken in order to confirm the synthesis pathway and identification of their tautomeric forms in the crystalline state. Theoretical calculations showed that the physico-chemicals (logP) and electronic properties (MEP distribution, energy localization of HOMO and LUMO orbitals) are related to observed antimicrobial activity of investigated compounds. The molecular docking study carried out for the most active against M. tuberculosis compound 3b using the M. tuberculosis cytochrome P450 CYP121 showed that this compound binds to the active site of P450 by hydrogen bonds via water molecule with the amino acid residue of Met86A and molecule of hem.

Synthesis of 1,6-hexanediyl-bis(semicarbazides) and 1,6-hexanediyl-bis(1,2, 4-triazol-5-ones) and their antiproliferative and antimicrobial activity

A series of 1,6-bis(3-substituted 1,5-dihydro-5-oxo-4H-1,2,4-triazol- -4-yl)hexanes 3a-g were synthesized by the cyclization reaction of 1,6-bis{[(2- -substituted hydrazinyl)carbonyl]amino}hexanes 2a-g in alkaline medium. The new derivatives 3a-c were screened in vitro for their antiproliferative and anticancer activity in human tumor cell lines derived from breast and lung carcinoma cells. Compounds 3a (at a concentration of 0.18 mM), 3b (at concentrations of 0.12 and 0.02 mM) and 3c (at concentrations of 0.23 and 0.11 mM) were found to be the most effective against the lung cell line. Compound 3a had the greatest antiproliferative effect on the breast carcinoma cell line. Representative compounds were established and evaluated as antimicrobial agents. All the tested derivatives showed minimum inhibitory concentrations (MIC) in the range 1.87-7.5 μg mL-1. Compound 3b was the most effective against Candida albicans (MIC 1.87 μg mL-1). Copyright 2012 (CC) SCS.

Synthesis, experimental and theoretical study on the structure of some semicarbazides with potential antibacterial activity

A series of 1,4-disubstituted semicarbazide and 4,4'-bis[1-substituted semicarbazide]diphenyl-methane derivatives were synthesized to explore their antibacterial activity. New compounds were characterized by elemental analysis and spectroscopic data. In order to find the tautomeric equilibrium for the molecules energy calculations for each possible tautomeric form of model compound 2, and for the most antibacterially active compound 7 in the investigated series, were calculated for the gas phase at the RHF/SCF/6-31G** level of theory.

Determination of the lipophilicity of some new derivatives of semicarbazide and 1,2,4-Triazol-5-one with potential antibacterial activity

The chromatographic behavior of new derivatives of 1,2,4-triazol-5-one and semicarbazide was determined. The lipophilicity was confirmed by the use of a RP-TLC method. The partition coefficients were calculated by use of theoretical procedures. The correl