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3-AMINO-2-MERCAPTO-3H-QUINAZOLIN-4-ONE is an organic compound belonging to the quinazoline family, characterized by its unique chemical structure featuring an amino group, a mercapto group, and a 3H-quinazolinone core. 3-AMINO-2-MERCAPTO-3H-QUINAZOLIN-4-ONE exhibits a wide range of biological activities and has potential applications in various fields due to its versatile chemical properties.

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  • 16951-33-0 Structure
  • Basic information

    1. Product Name: 3-AMINO-2-MERCAPTO-3H-QUINAZOLIN-4-ONE
    2. Synonyms: ZERENEX E/4047831;ART-CHEM-BB B020621;AKOS B020621;3-AMINO-2-MERCAPTO-3H-QUINAZOLIN-4-ONE;3-AMINO-2-MERCAPTOQUINAZOLIN-4-ONE;3-amino-2-thioxo-2,3-dihydroquinazolin-4(1H)-one;4(1H)-quinazolinone, 3-amino-2,3-dihydro-2-thioxo-;3-amino-2-thioxo-2,3-dihydroquinazolin-4(1H)-one hydrochloride
    3. CAS NO:16951-33-0
    4. Molecular Formula: C8H7N3OS
    5. Molecular Weight: 193.23
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 16951-33-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 371.6 °C at 760 mmHg
    3. Flash Point: 178.5 °C
    4. Appearance: /
    5. Density: 1.55 g/cm3
    6. Vapor Pressure: 1.02E-05mmHg at 25°C
    7. Refractive Index: 1.784
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: 3-AMINO-2-MERCAPTO-3H-QUINAZOLIN-4-ONE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 3-AMINO-2-MERCAPTO-3H-QUINAZOLIN-4-ONE(16951-33-0)
    12. EPA Substance Registry System: 3-AMINO-2-MERCAPTO-3H-QUINAZOLIN-4-ONE(16951-33-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 16951-33-0(Hazardous Substances Data)

16951-33-0 Usage

Uses

Used in Pharmaceutical Industry:
3-AMINO-2-MERCAPTO-3H-QUINAZOLIN-4-ONE is used as a key intermediate in the synthesis of various pharmaceutical compounds for its potential anti-HIV, antibacterial, and antifungal properties. The compound's unique structure allows for the development of new drugs that can target specific pathogens and viruses, offering novel treatment options for a range of diseases.
Used in Antiviral Applications:
In the field of antiviral research, 3-AMINO-2-MERCAPTO-3H-QUINAZOLIN-4-ONE is utilized for its potential anti-HIV activity. The compound's ability to inhibit the replication of the human immunodeficiency virus (HIV) makes it a promising candidate for the development of new antiretroviral drugs, which could help in the fight against acquired immunodeficiency syndrome (AIDS).
Used in Antibacterial Applications:
3-AMINO-2-MERCAPTO-3H-QUINAZOLIN-4-ONE is also used as a starting material for the development of new antibacterial agents. Its potential to combat bacterial infections, including those caused by drug-resistant strains, makes it a valuable compound in the ongoing battle against antibiotic resistance.
Used in Antifungal Applications:
Additionally, 3-AMINO-2-MERCAPTO-3H-QUINAZOLIN-4-ONE is employed in the development of antifungal agents, targeting various fungal pathogens responsible for a range of infections. The compound's ability to inhibit fungal growth and proliferation contributes to the development of new treatments for fungal diseases.

Check Digit Verification of cas no

The CAS Registry Mumber 16951-33-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,9,5 and 1 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 16951-33:
(7*1)+(6*6)+(5*9)+(4*5)+(3*1)+(2*3)+(1*3)=120
120 % 10 = 0
So 16951-33-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H7N3OS/c9-11-7(12)5-3-1-2-4-6(5)10-8(11)13/h1-4H,9H2,(H,10,13)

16951-33-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Amino-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

1.2 Other means of identification

Product number -
Other names 3-amino-2-sulfanylidene-1H-quinazolin-4-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:16951-33-0 SDS

16951-33-0Relevant articles and documents

Synthesis and Antioxidant Evaluation of Quinoxalino[2′,3′:5,6][1,3,4]thiadiazino[2,3-b]quinazolin-15-ones: Derivatives of a Novel Ring System

Mousavi, Mahsa,Bakavoli, Mehdi,Shiri, Ali,Eshghi, Hossein

, p. 517 - 521 (2018)

Quinoxalino[2′,3′:5,6][1,3,4]thiadiazino[2,3-b]quinazolin-15-one, a novel fused heterocyclic system, was synthesized from a one-pot condensation reaction of 2,3-dichloroquinoxaline and 3-amino-2-thioxo-2,3-dihydroquinazolin-4(1H)-one under mild condition. Derivatization was performed on treatment of the titled compound with several alkyl bromides. In vitro antioxidant activity of the synthesized compounds was evaluated.

Hg2+ mediated quinazoline ensemble for highly selective recognition of Cysteine

Anand, Thangaraj,Sivaraman, Gandhi,Chellappa, Duraisamy

, p. 18 - 24 (2014)

A fluorimetric sensor for Hg2+ ion and Cysteine based on quinazoline platform was designed and synthesized by one step reaction and characterized by using common spectroscopic methods. Time Dependent Density Functional Theory calculations shows that probe behaves as "ON-OFF" fluorescent quenching sensor via electron transfer/heavy atom effect. Receptor was found to exhibit selective fluorescence quenching behavior over the other competitive metal ions, and also the receptor-Hg2+ ensemble act as an efficient "OFF-ON" sensor for Cysteine. Moreover this sensor has also been successfully applied to detection of Hg2+ in natural water samples with good recovery.

Synthesis and reactivity of 1,2,4-triazolo[1,5-c]quinazolines

Pfeifer, Wolf-Diethard,Hetzheim, Annemarie,Pazdera, Pavel,Bodtke, Anja,Mücke, Jana

, p. 1327 - 1336 (1999)

The preparation of 1,2,4-triazolo[1,5-c]quinazolines 4a-d, 5, 8a-d by cyclocondensation of 1a-c with carboxylic acids and carboxylic anhydrides, respectively, is described. By different pathways, the 5-thioxo-5,6-dihydro- 1,2,4-triazolo[1,5-c]quinazolines

Quinazoline copper(II) ensemble as turn-on fluorescence sensor for cysteine and chemodosimeter for NO

Anand, Thangaraj,Sivaraman, Gandhi,Chellappa, Duraisamy

, p. 47 - 52 (2014)

A fluorescent quinazoline based chemosensor QHYN had been designed and synthesized. It exhibits high sensitivity and selectivity towards Cu 2+ over other metal ions in DMSO:H2O (1:9, v/v) at pH = 7.4 [HEPES buffer] by fluorescence quenching. Addition of nitric oxide to a solution of this QHYN·Cu(II) restores the fluorescence. This is attributed to the reduction of the Cu(II) centre by nitric oxide to diamagnetic Cu(I). The fluorescence response of QHYN·Cu(II) to NO is direct and specific, which is a significant improvement over commercially available small molecule-based chemodosimeter probe that are capable of detecting NO. The QHYN·Cu(II) also acts as an efficient off-on fluorescent sensor for cysteine with high sensitivity.

Synthesis of some quinazolinones inspired from the natural alkaloid L-norephedrine as EGFR inhibitors and radiosensitizers

Ghorab, Mostafa M.,Abdel-Kader, Maged S.,Alqahtani, Ali S.,Soliman, Aiten M.

, p. 218 - 237 (2021)

A set of quinazolinones synthesized by the aid of L-norephedrine was assembled to generate novel analogues as potential anticancer and radiosensitizing agents. The new compounds were evaluated for their cytotoxic activity against MDA-MB-231, MCF-7, HepG-2, HCT-116 cancer cell lines and EGFR inhibitory activity. The most active compounds 5 and 6 were screened against MCF-10A normal cell line and displayed lower toxic effects. They proved their relative safety with high selectivity towards MDA-MB-231 breast cancer cell line. Measurement of the radiosensitizing activity for 5 and 6 revealed that they could sensitize the tumour cells after being exposed to a single dose of 8 Gy gamma radiation. Compound 5 was able to induce apoptosis and arrest the cell cycle at the G2-M phase. Molecular docking of 5 and 6 in the active site of EGFR was performed to gain insight into the binding interactions with the key amino acids.

Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin derivatives with 3-amino-2-methylmercapto quinazolin-4(3H)-one

Pandeya,Sriram,Nath,De Clercq

, p. 11 - 17 (1999)

Isatin (Indole 2,3-dione), its 5-chloro and 5-bromo derivatives were added to 3-amino-2-methylmercapto quinazolin-4(3H)-one to form Schiff bases and the N-Mannich bases of these compounds were synthesized by reacting with formaldehyde and several secondar

QUINAZOLINE DERIVATIVES, COMPOSITIONS, AND USES RELATED THERETO

-

Page/Page column 40; 41, (2014/01/07)

The disclosure relates to quinazoline derivatives, compositions, and methods related thereto. In certain embodiments, the disclosure relates to inhibitors of NADPH-oxidases (Nox enzymes) and/or myeloperoxidase.

Synthesis of new 4(3H)-quinazolinone derivatives by reaction of 3-amino-2(1H)-thioxo-4(3H)-quinazolinone with selected chloroformates: Ammonolysis of 3-ethoxycarbonylamino-2-ethoxycarbonylthio-4(3h)-quinazolinone, part 21

Nawrocka, Wanda P.

experimental part, p. 261 - 274 (2009/09/25)

A series of N- and S-alkylated 4(3H)-quinazolinone derivatives (2-6) have been synthesized by the reaction of 3-amino-2(1H)-thioxo-4(3H)-quinazolinone (1) with selected chloroformates. 3-Ethoxycarbonylamino-2-ethoxycarbonylthio-4(3H)- quinazolinone (3) wa

NOVEL 2,3-DIAMINO-QUINAZOLINONE DERIVATIVES AND THEIR MEDICAL USE

-

Page/Page column 37, (2009/01/20)

This invention relates to novel 2,3-diamino-quinazolinone derivatives having medical utility, to use of the 2,3-diamino-quinazolinone derivatives of the invention for the manufacture of a medicament, to pharmaceutical compositions comprising the 2,3-diami

Synthesis and antihypertensive activity of novel 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones

Alagarsamy, Veerachamy,Pathak, Urvishbhai S.

, p. 3457 - 3462 (2008/02/07)

A series of 3-benzyl-2-substituted-3H-[1,2,4]triazolo[5,1-b]quinazolin-9-ones have been synthesized by the cyclocondensation of 3-amino-2-benzylamino-3H-quinazolin-4-one with a variety of one-carbon donors. The starting material 3-amino-2-benzylamino-3H-quinazolin-4-one was synthesized from methyl anthranilate by a novel innovative route. The title compounds were evaluated for their in vivo antihypertensive activity using spontaneously hypertensive rats (SHR). While all the test compounds exhibited significant antihypertensive activity, 3-benzyl-2-methyl-3H-[1,2,4]triazolo[5,1-b] quinazolin-9-one exhibited antihypertensive activity more than the reference standard prazocin.

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