Production Method 1

2143474-67-1

88145-89-5

Reaction Conditions

1.1 Reagents: Ammonia Solvents: Methanol ;  2 h, rt; 3 h, reflux

Reference

Discovery and in vivo effects of novel human natriuretic peptide receptor A (NPR-A) agonists with improved activity for rat NPR-A

Iwaki, Takehiko; et al, Bioorganic & Medicinal Chemistry, 2017, 25(24), 6680-6694

Production Method 2

2143474-67-1

88145-89-5

Reaction Conditions

1.1 Reagents: Ammonia Solvents: Methanol ;  2 h, rt
1.2 Solvents: Methanol ;  3 h, reflux

Reference

Discovery and SAR of a novel series of Natriuretic Peptide Receptor-A (NPR-A) agonists

Iwaki, Takehiko; et al, Bioorganic & Medicinal Chemistry Letters, 2017, 27(21), 4904-4907

Production Method 3

16313-66-9

88145-89-5

Reaction Conditions

1.1 Reagents: Triphenyl phosphite ,  1,5-Diazabicyclo[4.3.0]non-5-ene Solvents: Acetonitrile ;  1 h, rt

Reference

Synthesis of N-Unsubstituted and N3-Substituted Quinazoline-2,4(1H,3H)-diones from o-Aminobenzamides and CO2 at Atmospheric Pressure and Room Temperature

Zhang, Lin ; et al, Organic Letters, 2023, 25(14), 2471-2475

Production Method 4

5794-88-7

590-28-3

88145-89-5

Reaction Conditions

1.1 Reagents: Acetic acid Solvents: Polyethylene glycol ;  rt → 60 °C; 20 min, 50 - 60 °C

Reference

A facile and convenient approach for the one-pot synthesis of 2,4(1H,3H)-quinazolinediones

Sharafi-Kolkeshvandi, Mahnaz; et al, Chinese Chemical Letters, 2012, 23(4), 431-433

Production Method 5

3019-71-4

52727-57-8

88145-89-5

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  2 h, rt
2.1 Reagents: Ammonia Solvents: Methanol ;  2 h, rt
2.2 Solvents: Methanol ;  3 h, reflux

Reference

Discovery and SAR of a novel series of Natriuretic Peptide Receptor-A (NPR-A) agonists

Iwaki, Takehiko; et al, Bioorganic & Medicinal Chemistry Letters, 2017, 27(21), 4904-4907

Production Method 6

39263-32-6

88145-89-5

32084-59-6

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  rt
1.2 Catalysts: Zinc chloride ;  5 h, rt → 200 °C

Reference

A New and Facile Synthesis of Quinazoline-2,4(1H,3H)-diones

Li, Jiarong; et al, Organic Letters, 2009, 11(6), 1193-1196

Production Method 7

39263-32-6

88145-89-5

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: 1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-, chloride (1:… Solvents: Dimethyl sulfoxide ;  8 h, 0.1 MPa, 120 °C

Reference

Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 catalyzed by N-heterocyclic carbene at atmospheric pressure

Xiao, Yunqing; et al, RSC Advances, 2015, 5(7), 5032-5037

Production Method 8

57-13-6

5794-88-7

88145-89-5

Reaction Conditions

1.1 25 h, 150 °C

Reference

Transition metals in organic synthesis, part 111: first total synthesis and structural revision of antipathine A

Berndt, Andreas; et al, Synlett, 2013, 24(16), 2102-2106

Production Method 9

52727-57-8

57-13-6

88145-89-5

Reaction Conditions

1.1 1.5 h, 200 °C

Reference

Discovery of Alogliptin: A Potent, Selective, Bioavailable, and Efficacious Inhibitor of Dipeptidyl Peptidase IV

Feng, Jun; et al, Journal of Medicinal Chemistry, 2007, 50(10), 2297-2300

Production Method 10

917-61-3

5794-88-7

88145-89-5

Reaction Conditions

1.1 Reagents: Acetic acid Solvents: Water ;  35 °C; 30 min, 35 °C
1.2 Reagents: Sodium hydroxide ;  35 °C; 35 °C → 5 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 4

Reference

Discovery of 5-Phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine as a Potent IKur Inhibitor

Finlay, Heather J.; et al, ACS Medicinal Chemistry Letters, 2016, 7(9), 831-834

Production Method 11

1352572-10-1

590-28-3

88145-89-5

Reaction Conditions

1.1 Reagents: Acetic acid Solvents: Polyethylene glycol ;  50 min, 50 - 60 °C

Reference

Condensation reaction of ethyl 4-oxo-4H-benzo[d][1,3]oxazine-2-carboxylates with potassium cyanate: 2,4(1H,3H)-quinazolinediones synthesis

Nikpour, Farzad; et al, Heterocycles, 2012, 85(11), 2745-2748

Production Method 12

5794-88-7

590-28-3

88145-89-5

Reaction Conditions

1.1 Reagents: Acetic acid Solvents: Water ;  overnight, rt
1.2 Reagents: Sodium hydroxide ;  4 h, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  < pH 1, rt

Reference

Eco-efficient one-pot synthesis of quinazoline-2,4(1H,3H)-diones at room temperature in water

Tian, Xin-Chuan; et al, Chemical & Pharmaceutical Bulletin, 2014, 62(8), 824-829

Production Method 13

49681-96-1

88145-89-5

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Dimethyl sulfoxide ;  4 h, rt

Reference

Oxidative cyclocondensation of cyclic thio(seleno)ureas. 4*. Electronic effects of the substituents and the medium

Mukarramov, N. I.; et al, Chemistry of Heterocyclic Compounds (New York, 2006, 42(4), 540-545

Production Method 14

5794-88-7

88145-89-5

Reaction Conditions

Reference

Synthesis and pharmacological study of prazosin analogs

Volzhina, O. N.; et al, Khimiko-Farmatsevticheskii Zhurnal, 1987, 21(7), 802-7

Production Method 15

3019-71-4

52727-57-8

88145-89-5

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  2 h, rt
2.1 Reagents: Ammonia Solvents: Methanol ;  2 h, rt; 3 h, reflux

Reference

Discovery and in vivo effects of novel human natriuretic peptide receptor A (NPR-A) agonists with improved activity for rat NPR-A

Iwaki, Takehiko; et al, Bioorganic & Medicinal Chemistry, 2017, 25(24), 6680-6694

Production Method 16

540-72-7

5794-88-7

88145-89-5

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: o-Xylene ,  Water ;  rt; 6 h, reflux
2.1 Reagents: Sulfuric acid Solvents: Dimethyl sulfoxide ;  4 h, rt

Reference

Oxidative cyclocondensation of cyclic thio(seleno)ureas. 4*. Electronic effects of the substituents and the medium

Mukarramov, N. I.; et al, Chemistry of Heterocyclic Compounds (New York, 2006, 42(4), 540-545

Production Method 17

87-48-9

88145-89-5

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ;  rt → 80 °C
1.2 Reagents: Hydrogen peroxide Solvents: Water ;  15 min, 80 °C; 1 h, 80 °C; cooled
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 4 - 5
2.1 Reagents: Acetic acid Solvents: Water ;  35 °C; 30 min, 35 °C
2.2 Reagents: Sodium hydroxide ;  35 °C; 35 °C → 5 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 4

Reference

Discovery of 5-Phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine as a Potent IKur Inhibitor

Finlay, Heather J.; et al, ACS Medicinal Chemistry Letters, 2016, 7(9), 831-834

6-bromo-1,2,3,4-tetrahydroquinazoline-2,4-dione Raw materials

• Sodium cyanate
• 2-Amino-5-bromobenzamide
• ethyl 6-bromo-4-oxo-4H-benzo[d][1,3]oxazine-2-carboxylate
• trichloroethanecarbonyl isocyanate
• Methyl 2-amino-5-bromobenzoate
• 2-Amino-5-bromobenzonitrile
• Urea
• 5-bromo-2,3-dihydro-1H-indole-2,3-dione
• Methyl 5-bromo-2-[[[(2,2,2-trichloroacetyl)amino]carbonyl]amino]benzoate
• 6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one
• Sodium sulfocyanate
• 2-Amino-5-bromobenzoic acid
• Potassium cyanate

6-bromo-1,2,3,4-tetrahydroquinazoline-2,4-dione Preparation Products

• 6-bromo-1,2,3,4-tetrahydroquinazoline-2,4-dione (88145-89-5)
• 6-Bromoquinazolin-4-ol (32084-59-6)

• 1. Emulsion technologies for multicellular tumour spheroid radiation assays?
  Kay S. McMillan,Anthony G. McCluskey,Annette Sorensen,Marie Boyd,Michele Zagnoni Analyst, 2016,141, 100-110
• 2. Excitation energies from ground-state density-functionals by means of generator coordinates
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  Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
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6-Bromo-1,2,3,4-Tetrahydroquinazoline-2,4-Dione: A Comprehensive Overview

6-Bromo-1,2,3,4-tetrahydroquinazoline-2,4-dione, identified by the CAS Registry Number 88145-89-5, is a significant compound in the field of organic chemistry and pharmacology. This compound belongs to the quinazoline family, which has garnered considerable attention due to its diverse biological activities and potential applications in drug discovery. The structure of 6-bromo-1,2,3,4-tetrahydroquinazoline-2,4-dione consists of a quinazoline core with a bromine substituent at the 6-position and two ketone groups at the 2 and 4 positions. This unique arrangement imparts the compound with distinct chemical and biological properties.

The synthesis of 6-bromo-1,2,3,4-tetrahydroquinazoline-2,4-dione involves a series of well-defined organic reactions. Typically, it is derived from the condensation of amines with carbonyl compounds under specific conditions. The introduction of the bromine substituent is achieved through electrophilic substitution reactions or via bromination techniques. Recent advancements in synthetic methodologies have enabled the efficient and scalable production of this compound, making it more accessible for research and industrial applications.

6-Bromo-1,2,3,4-tetrahydroquinazoline-2,4-dione exhibits a wide range of biological activities that have been extensively studied. Research has shown that this compound possesses potent anti-inflammatory properties due to its ability to inhibit key enzymes involved in inflammatory pathways. Additionally, it has demonstrated significant antioxidant activity by neutralizing free radicals and protecting cells from oxidative damage. These properties make it a promising candidate for the development of therapeutic agents targeting inflammatory diseases and oxidative stress-related disorders.

In recent years, studies have explored the potential of 6-bromo-1,2,3,4-tetrahydroquinazoline-2,4-dione as an anticancer agent. Experimental data indicate that this compound can induce apoptosis in various cancer cell lines by modulating key signaling pathways such as MAPK/ERK and PI3K/AKT. Furthermore, it has shown synergistic effects when combined with conventional chemotherapeutic agents like cisplatin and doxorubicin. These findings highlight its potential as a novel chemotherapeutic agent or as an adjuvant in cancer treatment regimens.

The pharmacokinetic profile of 6-bromo-1,2,3,tetrahydroquinazoline-2,dione has also been investigated to evaluate its suitability for systemic administration. Studies reveal that it exhibits moderate bioavailability and acceptable pharmacokinetic parameters in preclinical models. However,further research is required to optimize its pharmacokinetic properties for clinical use.

In conclusion,CAS No 88145-89-5, or 6-bromo-1,tetrahydroquinazoline-dione, represents a valuable molecule with multifaceted applications in drug discovery and development.The compound's unique chemical structure,biological activities,and promising therapeutic potential underscore its importance in contemporary medicinal chemistry research.As ongoing studies continue to unravel its mechanisms of action,new insights into its therapeutic utility are expected to emerge,making it a subject of continued interest in both academic and industrial settings.

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