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4-Hydroxyquinazoline

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-H3001

  • Specification : 98%

  • CAS number : 491-36-1

  • Formula : C8H6N2O

  • Molecular Weight : 146.149

  • Volume : 25mg

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Catalogue Number

BF-H3001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

146.149

Appearance

Powder

Botanical Source

Strobilanthes cusia

Structure Type

Alkaloids

Category

SMILES

C1=CC=C2C(=C1)C(=O)N=CN2

Synonyms

IUPAC Name

Density

1.3±0.1 g/cm3

Solubility

Soluble to 10 mM in water and to 100 mM in DMSO

Flash Point

150.2±20.4 °C

Boiling Point

324.8±15.0 °C at 760 mmHg

Melting Point

216-219 °C(lit.)

InChl

InChI=1S/C8H6N2O/c11-8-6-3-1-2-4-7(6)9-5-10-8/h1-5H,(H,9,10,11)

InChl Key

QMNUDYFKZYBWQX-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:491-36-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31492051

Abstract

Previously unreported N,N’-ketal quinazolinone enantiomers [(-)-1 and (+)-1] and a new biogenetically related compound (2), along with six known compounds, 2-pyrovoylaminobenzamide (3), N-(2-hydroxypropanoyl)-2 amino benzoic acid amide (4), pseurotin A (5), niacinamide (6), citreohybridonol (7), citreohybridone C (8) were isolated from the ascidian-derived fungus Penicillium sp. 4829 in wheat solid-substrate medium culture. Their structures were elucidated by a combination of spectroscopic analyses (1D and 2D NMR and Electron Circular Dichroism data) and X-ray crystallography. The enantiomeric pair of 1 is the first example of naturally occurring N,N’-ketal quinazolinone possessing a unique tetracyclic system having 4-quinazolinone fused with tetrahydroisoquinoline moiety. The enantiomeric mixtures of 1 displayed an inhibitory effect on NO production in lipopolysaccharide-activated RAW264.7 cells, while the optically pure (-)-1 showed better inhibitory effect than (+)-1.

KEYWORDS

Penicillium; anti-inflammatory; ascidian-derived fungus; quinazolinone alkaloid.

Title

Penicamide A, A Unique N, N'-Ketal Quinazolinone Alkaloid from Ascidian-Derived Fungus Penicillium sp. 4829

Author

Senhua Chen 1 2, Minghua Jiang 3, Bin Chen 4, Jintana Salaenoi 5, Shah-Iram Niaz 6 7, Jianguo He 8, Lan Liu 9 10

Publish date

2019 Sep 5

PMID

31082683

Abstract

Thiazolidinediones and quinazolin-4-ones compounds, previously known for their activity against Type 2 diabetes and antifungal activity respectively, are currently being investigated for their anti-cancer activity. The determination of pharmacokinetic parameters for these two classes of compounds using a simultaneous chromatographic method with a low detection limit is a challenge. In this study, a highly sensitive and simultaneous LC-MS/MS-based bioanalytical method was developed and validated in rat plasma for the estimation of four novel anti-cancer compounds, BIT-15-67 and BNT-11, belonging to the Thiazolidinedione class, and BNUA-108 and BNUA-48, from the quinazolin-4-one class. The analytes were extracted from plasma samples by protein precipitation and separated on a short reverse phase Hypersil Phenyl BDS, 50 × 4.6 mm, 2.4 μm column at a column oven temperature of 40 °C. An isocratic mobile phase, a 20:80 (v/v) mixture of 5 mM ammonium acetate solution and acetonitrile containing 0.1% formic acid, was used for the elution at a flow rate of 0.4 mL/min. The analytes and internal standard, sulfaphenazole, were quantified in the multiple reaction monitoring mode using positive electrospray ionization with specific pair of mass by charge ratio. All standard validation parameters were assessed as per current bioanalytical method validation guidelines in rat plasma. The area response for the four analytes was found to be linear over the concentration range of 1.00 to 1000 ng/mL in rat plasma. The signal to noise at LLOQ of 1 ng/mL was adequate for application to different pre-clinical studies. The intra- and inter-day precision were <11% and accuracy deviated -1.8 to 9.60% from the nominal. The mean recovery was high (about 90%) and consistent for all the analytes over the linear dynamic range of the method. This simple, robust and validated method can be employed to determine the rat plasma concentrations of the four selected anticancer compounds in preclinical studies such as the pharmacodynamic and the pharmacokinetic studies including tissue distribution and excretion, and the toxicokinetic studies. In this study, pharmacokinetic parameters were determined using this method for all the four compounds individually following intravenous administration in rats.

KEYWORDS

Anti-cancer; LC-MS/MS; Quinazolin-4-one; Rat plasma; Thiazolidinedione.

Title

Validation of a sensitive simultaneous LC-MS/MS method for the quantification of novel anti-cancer thiazolidinedione and quinazolin-4-one derivatives in rat plasma and its application in a rat pharmacokinetic study

Author

Shankar Sengottuvelan 1, Ritika Uppal 2, Suneetha Vuppu 3

Publish date

2019 Jul 15

PMID

30884322

Abstract

Emergence of drug resistance has created unmet medical need for the development of new classes of antibiotics. Discovery of new antibacterial agents with new mode of action remains a high priority universally. 4(3H)-quinazolinone, a fused nitrogen heterocyclic compound has emerged as a biologically privileged structure, possessing a wide range of biological properties viz. anticancer, antibacterial, antitubercular, antifungal, anti-HIV, anticonvulsant, anti-inflammatory and analgesic activities. Promising antibacterial properties of quinazolinones have enthused the medicinal chemists to explore and develop this fused heterocyclic system for new antibacterial agents. Utilization of quinazolinone core for the design and synthesis of new antibacterial agents has recently gained momentum. This review aims to provide an overview of the structures and antibacterial activity of various 4(3H)-quinazolinone derivatives covering various aspects of in vitro and in vivo pharmacological activities and structure activity relationships (SARs).

KEYWORDS

4(3H)-Quinazolinone; Antibacterial agents; Cytotoxicity; Drug resistance; Minimum inhibitory concentration; Staphylococcus aureus.

Title

4(3H)-Quinazolinone derivatives: Promising antibacterial drug leads

Author

Srikanth Gatadi 1, T Vasanta Lakshmi 1, Srinivas Nanduri 2

Publish date

2019 May 15


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