32618-85-2|6-Nitroquinazoline-2,4-diol| Ambeed

Structure of 32618-85-2

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Quality Control of [ 32618-85-2 ] Purity: 95% SDS Specification

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Product Details of [ 32618-85-2 ]

CAS No. :	32618-85-2
Formula :	C₈H₅N₃O₄
M.W :	207.14
SMILES Code :	OC1=NC(O)=C2C=C([N+]([O-])=O)C=CC2=N1
MDL No. :	MFCD07437915
InChI Key :	TWJZVXRMXVNSIE-UHFFFAOYSA-N
Pubchem ID :	816982

Safety of [ 32618-85-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 32618-85-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	6.0
Num. H-bond donors	2.0
Molar Refractivity	52.41
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	112.06 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.84
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.33
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.95
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.48
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.22
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.28

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.39
Solubility	0.845 mg/ml ; 0.00408 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.28
Solubility	0.108 mg/ml ; 0.000519 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.57
Solubility	5.63 mg/ml ; 0.0272 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.62 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.82

Application In Synthesis of [ 32618-85-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 32618-85-2 ]

[ 32618-85-2 ] Synthesis Path-Downstream 1~35

1
[ 32618-85-2 ]
6-amino-1H-quinazoline-2,4-dithione [ No CAS ]

References: [1]Journal of the American Chemical Society,1949,vol. 71,p. 2279,2280.

2
[ 32618-85-2 ]
[ 74173-77-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tri-n-propylamine; trichlorophosphate; In toluene; at 20 - 110℃;	Step B: Preparation of 2,4-dichloro-6-nitro-quinazoline. Phosphorus oxychloride (6.64 mL, 72.6 mmol) was added to a suspension of 6-nitro-1 H-quinazoline-2,4-dione (5.01 g, 24.2 mmol) in toluene (100 mL) and the reaction mixture was heated to 55 C. Tri-n-propylamine (12.1 mL, 63.9 mmol) was added dropwise from an addition funnel over 25 minutes. The reaction mixture was heated to 110 C. for 6 h, stirred at room temperature for 4 d, and then pipetted into water (75 mL) and vigorously stirred for 1 h. The two layers were filtered and separated. The organic layer was washed with brine (30 mL), dried (MgSO4), and concentrated to yield the titled compound (3.79 g, 67% yield, 95% pure) after 24 h under high vacuum. This compound did not yield MS data. 1H NMR (600 MHz, CDCl3): 9.18 (d, J=2.4 Hz, 1H), 8.75 (dd, J=9.2, 2.5 Hz, 1H), 8.18 (d, J=9.2 Hz, 1H).
63%	With phosphorus pentachloride; trichlorophosphate; for 6.5h;Reflux;	The reaction mixture of compound 2a (0.78 g, 3.78 mmol), PCl5 (4.11 g, 19.7 mmol) and POCl3 (16 mL) was stirred at reflux for 6.5 h. The excess POCl3 was removed by evaporation. The residue was dissolved in ice water, and then the solution pH was adjusted to pH 5-6 with saturated NaHCO3. The water phase was extracted with EtOAc (60 mL × 5) and the organic layer was dried over anhydrous Na2SO4, concentrated to give the crude product which was purified by column chromatography on silica gel (petroleum ether/EtOAc = 40:1) to afford compound 3a as white solid (0.58 g, 63%); mp 122-124 C; 1H NMR (CDCl3) delta: 8.18 (d, J = 9.0 Hz, 1H), 8.76 (dd, J1 = 9.3 Hz, J2 = 2.1 Hz, 1H), 9.18 (d, J = 1.8 Hz, 1H).
63.5%		General procedure: 6-Nitroquinazoline-2,4 (1H, 3H) -dione (0.782 g, 3.78 mmol),Phosphorus pentachloride (4.111 g, 19.74 mmol),Add to 16 mL of phosphorus oxychloride,The reaction mixture was heated to reflux for 6.5 h and worked up as in Example 1 (b).0.585 g of a white solid was obtained in a yield of 63.5%. 1H-Quinazolin-2,4-one (0.5 g, 3.09 mmol) and phosphorus oxychloride (4.3 mL) were added to the reaction flask. After stirring for 0.5 h, 1.6 mL of N, N-dimethylaniline was added and the mixture was refluxed Reaction about 7h. The excess phosphorus oxychloride was distilled off under reduced pressure, and the remaining phosphorus oxychloride was taken out with chloroform. The residue was dissolved in ethyl acetate, and the excess N, N-dimethylaniline was removed with cold dilute hydrochloric acid to separate the water Phase, the organic phase was adjusted with saturated sodium bicarbonate pH = 5-6, the aqueous phase was extracted with ethyl acetate, the organic phase was combined, washed sequentially with saturated aqueous sodium chloride solution, the organic phase was dried over anhydrous magnesium sulfate, Mobile phase: ethyl acetate / petroleum ether = 50/1) to give crude product 0.649g. The crude product was recrystallized from 6 mL of methanol to give 0.489 g of a yellow flocculent solid. Yield: 79.6%.

58%	With phosphorus pentachloride; trichlorophosphate; at 120℃; for 4h;Inert atmosphere;	A suspension of 6-nitro-1 H-quinazoline-2,4-dione (3530 mg, 17.04 mmol) and PCIs (18826.5 mg, 88.62 mmol) in POCIs (24.1 ml, 255.62 mmol) was stirred at 120 C under N2 for 4 (0397) hours. Then reaction crude was concentrated to dryness at low pressure and purification by typical silica gel flash chromatography (cyclohexane/AcOEt from 95:5 to 80:20) afforded the pure title compound as white solid (2412 mg, yield 58 %). Rt= 2.1 6 min; MS (ESI) m/z: 244.3 [M-H]+, [M-H]+ calculated: 244.3. 1 H NMR (400 MHz, CDC ) delta 9.18 (d, J = 2.4 Hz, 1 H), 8.75 (dd, J = 9.2, 2.5 Hz, 1 H), 8.18 (d, J = 9.2 Hz, 1 H).
13%	With N,N-dimethyl-aniline; trichlorophosphate; at 110℃; for 5h;Inert atmosphere;	[00414] To a solution of 6-nitroquinazoline-2,4(lH,3H)-dione (34 g, 164.14 mmol) in POCl3 (150 mL) was added dimethyl-phenyl-amine (60 g, 492.42 mmol). The mixture was stirred at 110 C for 5 hours. The mixture was concentrated in vacuum and the remaining residue was neutralized by aq. NaHC03. The aqueous phase was extracted with EtOAc (80 mL x3). The organic phase was concentrated to dryness and the residue was purified by silica gel column chromatography (DCM: PE = 2: 1) to give 2,4-dichloro-6- nitroquinazoline (5 g, yield: 13 %) as a yellow solid.

References: [1]Patent: US2010/204226,2010,A1 .Location in patent: Page/Page column 61.
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2797 - 2807.
[3]Patent: CN102250075,2016,B .Location in patent: Paragraph 0395; 0414; 0415.
[4]Patent: WO2018/114700,2018,A1 .Location in patent: Page/Page column 22; 53.
[5]Patent: WO2015/200534,A2 .Location in patent: Paragraph 00414.
Patent: ,2015, .Location in patent: Paragraph 00414.
[6]Journal of the Chemical Society,1948,p. 1759,1765.
[7]Journal of the Chemical Society,1948,p. 1759,1765.
[8]Journal of Medicinal Chemistry,1995,vol. 38,p. 3547 - 3557.
[9]Patent: US6339089,2002,B2 .Location in patent: Referential example 3.
[10]Chemical and Pharmaceutical Bulletin,2015,vol. 63,p. 75 - 80.
[11]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 2755 - 2766.

3
[ 32618-85-2 ]
[ 76089-17-3 ]

References: [1]Journal of the American Chemical Society,1942,vol. 64,p. 2644,2646.

4
[ 3601-89-6 ]
[ 32618-85-2 ]
[ 192570-40-4 ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

5
[ 86-96-4 ]
[ 32618-85-2 ]

Yield	Reaction Conditions	Operation in experiment
82%		On an ice bath, 2 g (12,3 mmol) of quinazoline-2,4(1H,3H)-dione 2, were dissolved in 19 mL of sulfuric acid. Maintaining the mixture under agitation,a solution of 0.68 mL of nitric acid (12.3 mmol) and 1.37 mL of sulfuric acid were by dropwise added during 30 minutes and left reacting for 3 hours at 0C. After this time, the reaction mixture was poured into a beaker containing 70ml cold water. Subsequently, 70 ml of solution 9.5N of NaOH was dropwise added. The resulting precipitate was filtered at vacuum, dried and purified by chromatographic column using petroleum-ether/ethylacetate (3/7) as eluent.This gave 2.1 g (82% yield) of a yellow product.

References: [1]Journal of the Chilean Chemical Society,2013,vol. 58,p. 1817 - 1819.
[2]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

7
5-nitro-2-<ω-nitro-ureido>-benzoic acid methyl ester [ No CAS ]
[ 32618-85-2 ]

References: [1]Journal of the American Chemical Society,1919,vol. 41,p. 2061.

8
N_.N'-benzoylen-urea [ No CAS ]
[ 32618-85-2 ]

References: [1]Chemische Berichte,1869,vol. 2,p. 418 Anm. 2.
Journal fuer Praktische Chemie (Leipzig),1872,vol. <2> 5,p. 371.
[2]Journal of the American Chemical Society,1919,vol. 41,p. 2061.

9
[ 17420-30-3 ]
[ 124-38-9 ]
[ 32618-85-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With KCC-1/IL NPs; at 70℃; under 6000.6 Torr; for 1h;Autoclave;	General procedure: 2-aminobenzonitrile (1mmol), and KCC-1/IL NPs (0.0007g) were added. The autoclave was closed, purged twice with CO2 gas, pressurized with 0.8MPa of CO2 and then heated at 70C for 60min. Then the reactor was cooled to ambient temperature, and the resulting mixture was transferred to a 50mL round bottom flask. Upon completion, the progress of the reaction was monitored by TLC when the reaction was completed, EtOH was added to the reaction mixture and the KCC-1/IL NPs were separated by distillation under vacuum. Then the solvent was removed from solution under reduced pressure and the resulting product purified by recrystallization using n-hexane/ethyl acetate.
91%	With fibrous nanosilica functionalized with sodium tripolyphosphate and 3-aminopropyltriethoxysilane; In neat (no solvent); at 70℃; under 11251.1 Torr; for 0.833333h;Autoclave; Green chemistry;	General procedure: 2-aminobenzonitrile (1 mmol) and KCC-1/STPP NPs (0.7 mg) were mixed together. The autoclave was closed, purged twice with CO2 gas, pressurized to 1.5 MPa of CO2, and heated at 70C for 50 min. Then, the reactor was cooled to ambient temperature and the resulting mixture was transferred to a 50 mL round-bottom flask. During completion, the reaction progress was monitored by TLC. Following its completion, EtOH was added to the reaction mixture and the catalyst was separated by filtration. Afterwards, the solvent was removed from the solution under reduced pressure and the resulting product was purified by recrystallization using n-hexane/ethyl acetate. The products are known and their sample characterization data is presented in the Supplemental Materials.
81%	With {Eu[N(SiMe3)2](mu-O:kappa2-C6H5C(O)NC6H3(iPr)2)(THF)}2; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 100℃; for 24h;	Under anhydrous, anaerobic, argon protection, 0.0999 g (7.5 × 10 -5 mol){L2Eu [N (SiMe3) 2] · THF} 2, followed by 11.2 muL (7.5 × 10 -5 mol) of DBU,Under the protection of carbon dioxide bag, add 2mL dimethyl sulfoxide,After adding 0.3107 g (1.5 x 10-3 mol) of 2-amino-5-nitrobenzonitrile,The reaction was stirred in a constant temperature bath at 100 C. After 24 hours,The reaction was quenched by adding 5 mL of 2 mol / L hydrochloric acid and suction filtration. The solid was washed with 3 × 5 mL of hydrochloric acid, then with toluene and ether, the residual solvent was removed and the solid was dried to give the product in a yield of 81%

	1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; under 760.051 Torr;	SynthesisPeptidomimetics 37-44 were synthesized via solid phase peptide synthesis, using Suzuki couplings employing various boronic acids and aryl bromides. Intermediates display hydrophobic substituents from the aromatic spacer (Abz). The simple quinazoline scaffolds derived from commercially available starting materials. The synthesis of the quinazolines cores 45a-b was accomplished by the cyclization of 4-nitroanthranilic acid by the reaction with sodium isocyanate or cyclization employing a carbon dioxide atmosphere with catalytic DBU (1 ,8-diazabicyclo[5.4.0]undec-7-ene) from 4- and 5-nitro precursors respectively Figure 10. Alkylation was followed by reduction of the nitro group followed by coupling with A- nitrobenzoyl chloride via anilide formation to provide 48a-b. Reduction to the aniline, coupling with AcArg(Pmc)-OH, and deprotection of the guanidine protecting group afforded 50a-b.A convergent synthesis using methyl-4-amino-2-bromobenzoate or methyl-4-aminobenzoate and 4-nitroaniline created non-peptidic inhibitors 56aa-ci, as seen in Figure 13. Suzuki coupling of the bromoaniline with the corresponding boronic acid, employing PdCI2(dppf) as a catalyst, created compounds 51a followed by reductive amination utilizing N-Boc- aminoacetaldehyde produced compounds 52a-c. A series of deprotections followed by guanidinylation of the resulting amine afforded the N-terminal portions of the inhibitor 53a-c. The C-terminal hydrophobic portion of the molecule was synthesized via alkylation of A- nitroaniline with the corresponding bromide and subsequent reduction of the nitro group utilizing tin (II) chloride, producing compounds 55a-i. Coupling of compounds 53a-c and 55a- i followed by Boc deprotection under acidic conditions produced inhibitors 56aa-ci. Inhibitors64a-b were derived from a similar synthesis, but in place of the reductive amination step, 48c was reacted with Boc-Gly-OH to provide the amide intermediate compound 62 which was manipulated in a similar manner to provide inhibitors 64a-b, seen in Figure 16.The synthesis of inhibitors 57aa-fa was designed to employ a late stage Suzuki coupling to provide faster access to a number of derivatives at the R1 position, while keeping R2 as a <n="13"/>benzyl substituent, see Figure 15. Commercially available methyl-4-amino-3-bromobenzoate was saponified under basic conditions followed by amide bond formation with compound 55a to provide compound 59a. This intermediate was then reacted with different boronic acid derivatives PdCI2(dppf) as a catalyst to provide 60aa-fa. A series of functional group transformations provided inhibitors 57aa-fa. The indole scaffold was readily derived from commercially available 4-iodoaniline and Boc- GIy-OH, which were reacted to form iodo-amide compound 65, seen in Figure 17. Sonagashira cross-coupling of compound 65 and ethynyl-trimethyl-silane (TMS-acetylene) followed by removal of the silyl protecting group afforded terminal alkyne compound 66. A consecutive Sonagashira cross-coupling with 2-iodo-4-nitroaniline followed by cycloisomerization employing catalytic copper (II) acetate41 afforded indole scaffold compound 68. Reduction of the nitro to the amine followed by alkylation with the cooresponding bromide provided compound 70a-b. A series of functional group transformations, similar to the reactions depicted in Figures 10 and 13, provided inhibitors 71a-b. It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention which, as a matter of language, might be said to fall therebetween. Now that the invention has been described,
		(1) DBU(32.7 g) was added to a solution of 2-amino-5-nitrobenzonitrile(11.69 g) in DMF(135 mL) at room temperature and the mixture was stirred under carbon dioxide atmosphere at room temperature overnight. The reaction solution was cooled to 0C, and 1N hydrochloric acid(1350 mL) was added dropwise. The precipitated crystals were filtered, washed with diethyl ether and dried to give 6-nitro-1H-quinazolin-2,4-dione(14.13 g) as a yellow powder. APCI-MS(m/e):206[M-H]-.

References: [1]Catalysis Communications,2015,vol. 72,p. 91 - 96.
[2]Catalysis science and technology,2016,vol. 6,p. 1435 - 1441.
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2018,vol. 193,p. 535 - 544.
[4]Tetrahedron,2002,vol. 58,p. 3155 - 3158.
[5]RSC Advances,2015,vol. 5,p. 24670 - 24674.
[6]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 1764 - 1771.
[7]European Journal of Organic Chemistry,2016,vol. 2016,p. 2555 - 2559.
[8]Patent: CN105153048,2017,B .Location in patent: Paragraph 0120; 0121.
[9]Green Chemistry,2014,vol. 16,p. 3142 - 3148.
[10]ChemCatChem,2016,vol. 8,p. 244 - 250.
[11]Heteroatom Chemistry,2012,vol. 23,p. 276 - 280.
[12]Catalysis science and technology,2014,vol. 4,p. 1608 - 1614.
[13]ChemSusChem,2017,vol. 10,p. 1145 - 1151.
[14]Tetrahedron Letters,2004,vol. 45,p. 7073 - 7075.
[15]Patent: WO2008/70823,2008,A2 .Location in patent: Page/Page column 4-5; 10-11; 6/14.
[16]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 153 - 157.
[17]Patent: EP1970373,2008,A1 .Location in patent: Page/Page column 44.
[18]Inorganic Chemistry,2012,vol. 51,p. 13001 - 13008.
[19]RSC Advances,2016,vol. 6,p. 111079 - 111089.

10
[ 174313-63-4 ]
[ 32618-85-2 ]

References: [1]Chemistry of Heterocyclic Compounds,2006,vol. 42,p. 540 - 545.

11
[ 80195-33-1 ]
[ 32618-85-2 ]

References: [1]Chemistry of Heterocyclic Compounds,2006,vol. 42,p. 540 - 545.

12
[ 74173-77-6 ]
[ 32618-85-2 ]

References: [1]Chemistry of Heterocyclic Compounds,2006,vol. 42,p. 540 - 545.

13
[ 32618-85-2 ]
1-{2-deoxy-3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl}-6-nitro-quinazoline-2,4(3H)-dione [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

14
[ 32618-85-2 ]
[ 192570-60-8 ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

15
[ 32618-85-2 ]
[ 192570-55-1 ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

16
[ 32618-85-2 ]
1-(2-deoxy-α,β-D-erythro-pentofuranosyl)-6-nitro-quinazoline-2,4(3H)-dione [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

17
[ 32618-85-2 ]
1-(2-deoxy-α-D-erythro-pentofuranosyl)-6-nitro-quinazoline-2,4(3H)-dione [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

18
[ 32618-85-2 ]
1-(2-deoxy-α-D-erythro-pentofuranosyl)-6-nitro-quinazoline-2,4(3H)-dione [ No CAS ]

References: [1]Tetrahedron,1997,vol. 53,p. 8457 - 8478.

19
[ 32618-85-2 ]
2-chloro-4-bennzylamino-6-nitroquinazoline [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3547 - 3557.

20
[ 32618-85-2 ]
Benzyl-(2-imidazol-1-yl-6-nitro-quinazolin-4-yl)-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3547 - 3557.

21
[ 32618-85-2 ]
N,N-diethyl-N'-(2-chloro-6-nitro-quinazolin-4-yl)-ethylenediamine [ No CAS ]

References: [1]Journal of the Chemical Society,1948,p. 1759,1765.

22
[ 869-07-8 ]
[ 32618-85-2 ]
[ 373-88-6 ]
[ 107-11-9 ]
[ 221042-30-4 ]