Synthesis and Bronchodilatory Activities of New Pyrazolo[4,3-d]pyrimidin-7-ones

Twelve novel pyrazolo [4,3-d] pyrimidin-7-ones were synthesized and their structures were confirmed by IR, 1H NMR and MS. Their in vitro bronchodilatory activities were tested in guinea-pigs. The pharmacological results show that compound 11c has more potent activity than aminophylline.

Syntheses and Vasodilatory Activities of New Pyrazolo[4,3-d]pyrimidin-7-ones

A series of novel pyrazolo [ 4,3-d ] pyrimidin-7-ones was designed and synthesized in order to find new potent phosphodiesterase 5 inhibitors（PDE5）. The structures of all the compounds were confirmed by IR, ^1H NMR and MS; their in vitro vasodilatory activities were tested on isolated rabbit aortic spiral strips. Among them, compound X3 displays a significant vasodilatory activity, which is more potent than verapamil.

A novel and convenient synthesis of thiazolo[3,2-a]pyrimidin-7-ones and pyrido[1,2-a]pyrimidin-2-ones using Vilsmeier reagent

A novel route for the synthesis of thiazolo[3,2-a]pyrimidin-7-ones and pyrido[1,2-a]pyrimidin-2,ones from acetylated 2- aminothiazoles and 2-aminopyridines under Vilsmeier conditions has been developed. The plausible mechanism has also been proposed.

7-Deazapurines:Synthesis of new pyrrolo[2,3d]pyrimidin-4-onescatalyzed by a Brφnsted-acidic ionic liquid as a green and reusable catalyst

Some new 2-aryl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-ones have been prepared through cyclocondensation of 2-amino 1H-pyrrole-3-carboxamides with aromatic aldehydes followed by air oxidation in the presence of 3-methyl-1-（4-sulfonic acid）butylimidazolium hydrogen sulfate[（CH;）;SO;HMIM][HSO;],a Br（?）nsted-acidic ionic liquid,as a green and reusable catalyst in solvent-free conditions.

A Solution-Phase Parallel Synthesis of 5-Substituted 3,6-Dihydro-7H-1,2,3-triazolo[4,5-dJpyrimidin-7-ones

5-Substituted 7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones （4） were rapidly prepared by a solution-phase parallel synthetic method, which includes aza-Wittig reaction of iminophosphorane （1） with phenyl isocynate to give car- bodiimide （2） and subsequent reaction of 2 with various amine and alcohols in the presence of catalytic amount of sodium alkoxide in a parallel fashion.

Efficient Synthesis of 3,5,6,7-Tetrahydro-4H-cyclopenta [4,5] thieno [2,3-d] Pyrimidin-4-ones

The title compounds 3,5,6,7-tetrahydro-4H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-ones（6） were synthesized by base catalytic reactions of secondary amines with carbodiimides 4, which were obtained from the aza-Wittig reaction of iminophosphoranes（3） with aromatic isocyanates.

A Selective Synthesis of 2-Alkylamino-5, 6, 7, 8-tetrahydro-benzothieno[2, 3-d]pyrimidin-4(3H)-ones

Alkylamino-5, 6, 7, 8-tetrahydrobenzothieno [2, 3-d] pyrimidin-4(3H)-ones 7 weresynthesized by a new selective synthetic method, which includes aza-Wittig reaction of imino-phosphorane 4 with aromatic isocynate to give carbodiimide 5 and subsequent reaction of 5 withvarious aliphatic primary amine in the presence of EtO-Na+.

The Synthesis of 7-[1-Aza-2-(dimethylamino)vinyl]-4-methylhydroquinolin-2-ones and their Isomerism in Different Solvents

The reaction of 7-amino-4-methyl-2(1H)-quinolone 1 and its 6-methyl derivative 2 with Vilsmeier reagent (DMF and POCl3) afforded 7-[1-aza-2-(dimethylamino)vinyl]-4-methyl-hydroquinolin-2-one 3 and 7-[1-aza-2-(dimethylamino)vinyl]-4,6-dimethylhydroquinolin- 2-one 4, respec-tively. H-1-NMR analysis in different solvents indicated that isomerism occurred due to hindered rotation around the (CH3)(2)N-C:N o -bond. The rotational energy barrier of 3 was calculated.

A rapid synthesis of isoxazolo[5,4-d]pyrimidin-4(5H)-ones under microwave irradiation with solid acid catalysis in solvent-free conditions

A rapid and efficient method for the synthesis of isoxazolo[5,4-d]pyrimidin-4（5H）-ones has been developed through cyclocondensation of 5-aminoisoxazole-4-carboxamides with orthoesters under conventional heating and solvent-free microwave irradiation with solid acid catalysis. In comparison, the reactions are faster and the yields are higher under microwave irradiation.

Efficient synthesis of 5,6-dihydrothieno[3′,2′:4,5]-thieno[2,3-d]pyrimidin-4(3H)-ones via an iminophosphorane

5,6-Dihydrothieno[3＇,2＇：4,5]thieno[2,3-d]pyrimidin-4（3H）-ones 6 were synthesized in yields of 71-87% by a consecutive method, which includes aza-Wittig reaction of iminophosphorane 3 with aromatic isocynate to give carbodiimide 4 and subsequent reaction of 4 with various amines, phenols or alcohols in the presence of catalytic amount of sodium ethoxide or solid potassium carbonate. 2009 Ming Wu Ding. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

Synthesis and Crystal Structure of 3-Benzyl-5-cyclohexylamino-6-phenyl-3,6-dihydro-1,2,3-triazolo[4,5-d]pyrimidin-7-one

The title compound 3-benzyl-5-cyclohexylamino-6-phenyl-3,6-dihydro-1,2,3- triazolo[4,5-d]pyrimidin-7-one (C23H24N6O, Mr = 400.48) has been synthesized by means of tandem aza-Wittig reaction, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n with a = 6.5550(6), b = 10.3711(10), c = 31.265(3) ?, β = 93.827(2)o,V = 2120.8(4) ?3, Z = 4, Dc = 1.254 g/cm3, S = 1.025, μ(MoKa) = 0.081 mm-1, F(000) = 848, R = 0.0576 and wR = 0.1368. X-ray analysis reveals that all ring atoms in the triazolopyrimidinone moiety are almost coplanar and the cyclohexyl ring adopts a chair confor- mation.

An Efficient Approach to 6, 7-Disubstituted-1H-quinoxalin-2-ones

A novel approach to the synthesis of 6, 7-disubstituted-1H-quinoxalin-2-ones is described.The title compounds were regioselectively prepared by starting from substituted phenylamines andchloroacetyl chloride through the efficient sequence of acylation, nitration, reduction, intramolecular alkylation, and oxidation.

Efficient Synthesis of 3,5,6,8-Tetrahydro-4H-thiopyrano[4′,3′:4,5]· thieno[2,3-d]pyrimidin-4-ones via an Iminophosphorane

3,5,6,8-Tetrahydro-4H-thiopyrano[4＇,3＇：4,5]thieno[2,3-d]pyrimidin-4-ones（7） were synthesized via the base catalytic reactions of amines or phenols with carbodiimides（5）, which were obtained from the aza-Wittig reac tions of iminophosphoranes（4） with aromatic isocyanates.

UPLC-MS/MS法测定槲寄生抗肿瘤成分1,7-bis(4-hydroxyphenyl)-1,4-heptadien-3-one的含量

目的建立超高效液相色谱-串联质谱法(UPLC/MS/MS)测定槲寄生中具有抗肿瘤活性的新化合物1,7-bis(4-hydroxyphenyl)-1,4-heptadien-3-one(BHPHD)的含量,并通过多因素方差分析比较产地与寄主对药材抗肿瘤成分含量的影响。方法以Thermo Hypersil GOLD C18(50 mm×2.1 mm,1.9μm)为分离色谱柱,乙腈-体积分数0.1%甲酸水溶液为流动相,流速0.2 m L·min-1,梯度洗脱,质谱检测器,电喷雾正离子,多反应监测模式,监测离子对m/z 295.09→106.99。结果BHPHD在质量浓度为0.050~2.5 mg·L-1内线性关系良好,精密度、重复性、稳定性试验的RSD均≤3.5%,平均加样回收率(n=9)为97.2%(RSD=1.6%)。结论该方法可满足定量要求。多因素方差分析表明槲寄生中BHPHD的含量受产地影响较大(P<0.01),受寄主影响不大。

Synthesis and Crystal Structure of 2-Ethoxy-3-n-butyl-benzofuro [2,3-d]pyrimidin-4(3H)-one

The crystal structure of the new title compound 2-ethoxy-3-n-butyl- benzofuro[2,3d]pyrimidin-4（3H）-one （C16H18N2O3, Mr = 286.32） has been prepared and determined by singlecrystal X-ray diffraction. The crystal is of monoclinic, space group P21/c with a = 13.7167（14）, b = 13.113（1）, c = 8.378（1） A, β = 98.992（2）^o, V = 1488.4（3） A^3, Z = 4, Dc = 1.278, F（000） = 608, μ = 0.089 mm^-1, MoKa radiation （2 = 0.71073）, R = 0.0498, wR = 0.1238 for 2336 observed reflections with I 〉 2σ（I）. X-ray diffraction analysis reveals that all ring atoms in the benzo[4, 5]furo [2,3-d] pyrimi- dinone moieties are almost coplanar.

Synthesis and Crystal Structure of(Z)-2-Methyl-5,6-dihydrobenzo[d]thiazol-7(4H)-one O-Prop-2-yn-1-yl Oxime Derivatives

Compound（Z）-2-methyl-5,6-dihydrobenzo[d]thiazol-7（4H）-one O-prop-2-yn-1-yl oxime, C11H12N2 OS, as a synthetic precursor of cytotoxic triazoles has been prepared and characterized by NMR spectra. Meanwhile, the crystal of IV was obtained and determined by X-ray single-crystal diffraction. Crystal data： monoclinic system, space group P21/c, a = 9.725（9）, b = 8.068（7）, c = 14.452（13）A, β = 98.68（2）°, V = 1120.9（17）A3, Z = 4, F（000） = 464, Dc = 1.305 g/cm^3, μ = 0.263 mm^-1, R = 0.0457 and w R = 0.1298 for 11511 independent reflections（Rint = 0.0709） and 2289 observed ones（I 〉 2σ（I））.

Synthesis and Crystal Structure of 1-(4-Fluorophenyl)-2-hexylthiobenzo[4,5]-furo[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5(1H)-one

The crystal structure of the title compound 1-（4-fluorophenyl） -2-hexylthio-benzo [4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidin-5（1H） -one（C23H21FN4O2S,Mr = 436.5） has been prepared and determined by single-crystal X-ray diffraction. The crystal is of monoclinic,space group P21/n with a = 13.9854（3） ,b = 17.2678（4） ,c = 18.1828（5）A,β = 99.364（2） °,V = 4332.58（18） A^3,Z = 4,Dc = 1.338,F（000） =1824,μ = 0.185 mm^-1,MoKa radiation（λ = 0.71073） ,R = 0.0538 and wR = 0.1162 for 4728 observed reflections with I 〉 2σ（I） . X-ray diffraction analysis reveals the fused rings of benzo[4,5]furo[3,2-d]-1,2,4-triazolo[1,5-a] pyrimidin-5（1H） -one system are nearly coplanar. The crystal packing is mainly stabilized by weak intermolecular C-H···O hydrogen bond and π-π interactions.

Synthesis and Crystal Structure of 2-(4’-Methylphenoxy)-5,8,9-trimethyl-3-phenyl Thieno[3′,2′:5,6]pyrido[4,3-d]pyrimidin-4-(3H)-one Hydrochloride

The title compound 2-（4＇-methylphenoxy）-5,8,9-trimethyl-3-phenyl thieno[3＇,2＇：5,6] pyrido[4,3-d]pyrimidin-4（3H）-one hydrochloride （C26H23Cl4N3O2S, Mr = 583.33） has been determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c with a = 14.8442（ 11 ）, b = 11.5131 （8）, c = 17.2010（13） A, β = 113.7250（10）°, V = 2691.3（3） ,A^3, Z = 4, Dc = 1.440 g/cm^3, S = 1.094,μ = 0.547 mm^-1, F（000） = 1200, the final R = 0.0571 and wR = 0.1458. X-ray analysis reveals that the title compound combines with a molecule of dichloromethane by an intramolecular hydrogen bond. The thienopyridine ring is almost coplanar, and the dihedral angle between the thiophene plane and the pyridine plane is 0.6°.

Synthesis and Structure of 6-(4-Fluorobenzylamino)-3-methylthio-1,5-diphenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

The title compound (C25H20FN5OS) has been synthesized and its crystal structure was determined by X-ray analysis. The crystal belongs to the orthorhombic system, space group Pbca with a = 10.327(4), b = 20.307(7), c = 21.234(9) ? α = 90, β = 90, γ = 90, V = 4453(3) 3, Z = 8, Dc = 1.365 g/cm3, Mr = 457.52, μ = 0.182 mm-1, F(000) = 1904, the final R = 0.0600 and wR = 0.0932 for 3911obsered reflections with I≥2σ(I). In the title compound, the S(1), C(1), C(2), C(3), C(4), C(5), N(1), N(2), N(3), N(4), O(1) and N(5) atoms form a mean planeⅠroughly within the average deviation of 0.0207 ? The dihedral angles between planesⅠandⅡ(C(19)C(20) C(21)C(22)C(23)C(24)),Ⅲ(C(6)C(7)C(8)C(9)C(10)C(11)) and Ⅳ(C(12)C(13)C(14) C(15)C(16)C(17)C(18)F(1)) are 21.40, 84.00 and 75.88, respectively.

Synthesis and Vasodilatory Activities of New Pyrazolo[3,4-d] pyrimidin-4-one Derivatives

A series of pyrazolo[3,4-d]pyrimidin-4-one derivatives were synthesized and tested for vasodilatory activities. All of them were new compounds and their structures were confirmed by IR, 1H NMR, MS and elemental analysis.