Acetamide

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Acetamide
Category Others
Catalog number BBF-04183
CAS 60-35-5
Molecular Weight 59.07
Molecular Formula C2H5NO
Purity > 98 %

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Description

Acetamide is the simplest amide derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent. Acetamide (2.88 g/kg/d) can reduce central nervous lesions, but the efficacy is not improved after increasing the dose.

Specification

Synonyms Ethanamide; Acetic Acid Amide; Methanecarboxamide; Acetimidic Acid; Amide C2
Storage Store at 2-8 °C
IUPAC Name acetamide
Canonical SMILES CC(=O)N
InChI InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
InChI Key DLFVBJFMPXGRIB-UHFFFAOYSA-N
Source This is an endogenously produced metabolite found in the human body.

Properties

Appearance White crystalline solid
Boiling Point 221 °C
Melting Point 78-81 °C
Density 1.159 g/cm3
Solubility Soluble in Water
LogP -1.26

Toxicity

Carcinogenicity 2B, possibly carcinogenic to humans.

Reference Reading

1. Design, synthesis and biological evaluation of 1,3,4-triazole-3-acetamide derivatives as potent neuraminidase inhibitors
Lin Shi, Xing Yong Zhang, Li Ping Cheng Bioorg Med Chem Lett. 2022 Apr 1;61:128590. doi: 10.1016/j.bmcl.2022.128590. Epub 2022 Jan 30.
Neuraminidase (NA) is an ideal target for the development of anti-influenza drugs. In this paper, ZINC06057848 was screened out as a hit compound by docking-based virtual screening and molecular dynamics (MD) simulation. The modification and optimization of hit ZINC06057848 resulted in the discovery of a series of novel 1,3,4-triazole-containing NA inhibitors (5a-5j). Compound 5c exerts the best inhibitory activity (IC50 = 0.11 µM) against NA, which is comparable to the positive control oseltamivir carboxylate (OSC) (IC50 = 0.10 µM). Molecular docking analysis indicates that the good efficacy of inhibitor 5c may be attributed to the furan and triazole rings extending into 430-cavity and the ethylbenzene part occupying the active site. The results of this work may help in the development of new NA inhibitors.
2. Discovery and computational studies of 2-phenyl-benzoxazole acetamide derivatives as promising P2Y14R antagonists with anti-gout potential
Mengze Zhou, Weiwei Wang, Zhongkui Wang, Yilin Wang, Yifan Zhu, Zhiqian Lin, Sheng Tian, Yuan Huang, Qinghua Hu, Huanqiu Li Eur J Med Chem. 2022 Jan 5;227:113933. doi: 10.1016/j.ejmech.2021.113933. Epub 2021 Oct 19.
The P2Y14 nucleotide receptor, a subtype of P2Y receptors, is implicated in many human inflammatory diseases. Based on the identification of favorable residues of two screening hits in the almost symmetrical P2Y14 binding domain, we describe the structural optimization of previously identified virtual screening hits 6 and 7 that result in the development of P2Y14R antagonists with a novel 2-phenyl-benzoxazole acetamide chemical scaffold. Notably, compound 52 showed potent P2Y14R antagonistic activity (IC50 = 2 nM), and a stronger inhibitory effect on MSU-induced inflammatory in vitro, better than a previously described P2Y14R antagonist PPTN. In vivo evaluation demonstrated that compound 52 also had satisfactory inhibitory activity on the inflammatory response of gout flares in mice. Moreover, P2Y14R antagonist 52 decreased paw swelling and inflammatory cell infiltration through cAMP/NLRP3/GSDMD signaling pathways in MSU-induced acute gouty arthritis mice. The discussions on the binding mechanism that employ MM/GBSA free energy calculations/decompositions also provide some useful clues for further structural designing of compound 52. Taken together, 2-phenyl-benzoxazole acetamide derivative 52 with potent P2Y14R antagonistic activity and in vivo potency could be a promising strategy for gout therapy and deserves further optimization.
3. Intrinsic acetamide brush-off by polyurea biodendrimers
Nuno Martinho, Rita F Pires, Mire Zloh, Vasco D B Bonifácio J Mater Chem B. 2021 Apr 21;9(15):3371-3376. doi: 10.1039/d1tb00105a. Epub 2021 Apr 6.
The presence of genotoxic impurities in active pharmaceutical ingredients (APIs) is a major concern for the pharmaceutical industry. Acetamide is a common genotoxic byproduct found in synthetic routes of many APIs, mainly due to acetonitrile hydrolysis, and selective scavenging is a still a challenging task. Herein, as a proof-of-concept, we evaluate polyurea (PURE) biodendrimers as strategic nanopolymers to prepare safe drug nanoformulations from mixtures containing acetamide, using (S)-ibuprofen (IBF) as a model drug. Furthermore, computational molecular dynamics (MD) simulations were conducted to rationalize in vitro results and to identify the key intermolecular interactions within mixtures. Experimental data were corroborated by MD simulations which showed that acetamide, IBF and carboxyfluorescein interactions with PURE biodendrimers are mostly at the surface. Also, PURE nanoformulations appear to be driven by hydrogen bonding, electrostatic and hydrophobic interactions.

Spectrum

GC-MS Spectrum - EI-B (Non-derivatized)

Experimental Conditions

Instrument Type: EI-B
Ionization Mode: positive
Chromatography Type: GC

Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive

Experimental Conditions

Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C2H5NO
Molecular Weight (Monoisotopic Mass): 59.0371 Da
Molecular Weight (Avergae Mass): 59.0672 Da

LC-MS/MS Spectrum - QqQ 7V, positive

Experimental Conditions

Instrument Type: QqQ
Collision Energy Level: low
Collision Energy Voltage: 7
Ionization Mode: positive

Predicted LC-MS/MS Spectrum - 10V, Negative

Experimental Conditions

Ionization Mode: Negative
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C2H5NO
Molecular Weight (Monoisotopic Mass): 59.0371 Da
Molecular Weight (Avergae Mass): 59.0672 Da

Mass Spectrum (Electron Ionization)

1H NMR Spectrum

Experimental Conditions

Solvent: D2O
Instrument Type: JEOL
Nucleus: 1H
Frequency: 90 MHz
Chemical Shift Reference: TSP

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