- One-step synthesis of lumazine and xanthine: First co-crystal of lumazine and perchloric acid with a unique monohydrated hydronium ion (H 5O2+) mediated supramolecular assembly of the lumazine dimer
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A perchloric acid mediated one-step synthesis of lumazine derivatives from pterins and xanthine from guanine is reported. However, 2-pivaloylamino derivatives of pterins underwent simple hydrolysis of the pivaloylamino group generating free pterin compounds, but the 2-oxo derivatives, that is, the lumazine compounds, were not obtained. A novel supramolecular assembly is constructed by the unique hydrogen bonding of H5O2 + bridging two hydrogen-bonded dimers of lumazine to form the co-crystal 21 with aqueous perchloric acid. In contrast, N2-pivaloyl- 6-bromo-5-deazapterin was simply hydrolysed to form the protonated deazapterin 22, which forms a unique six-membered cyclic hydrogen-bonded structure leading to the generation of a polymeric supramolecular assembly. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Goswami, Shyamaprosad,Maity, Annada C.,Fun, Hoong-Kun
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- Synthesis, characterization, crystal structure and DFT study of a new compound 3-(4-(2,4-dimorpholinopyrido[2,3-d]pyrimidin-6-yl)phenyl)-1,1-diethylurea
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In this study, the compound 3-(4-(2,4-dimorpholinopyrido[2,3-d]pyrimidin-6-yl)phenyl)-1,1-diethylurea was prepared. The synthesis of the compound was confirmed using 1H NMR, 13C NMR, HRMS and FT-IR spectroscopies. The crystal structure of the title compound was optimized using by density functional theory (DFT) calculations, and the molecular structure of the crystal was compared with theoretical calculations. The results show that the molecular structure optimized by DFT is essentially identical to the crystal structure determined by X-ray single-crystal diffraction. Additionally, the optimal structure and frontier orbital energy were calculated using DFT.
- Dai, Hongyu,Deng, Liyuan,Liao, Wanpeng,Liu, Tong,Wu, Feng,Zhao, Chunshen,Zhou, Zhixu
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- Synthesis, crystal structure and DFT study of a novel compound N-(4-(2,4-dimorpholinopyrido[2,3-d]pyrimidin-6-yl)phenyl)pyrrolidine-1-carboxamide
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In this paper, the compound N-(4-(2,4-dimorpholinopyrido[2,3-d]pyrimidin-6-yl)phenyl) pyrrolidine-1-carboxamide was synthesized and characterized using 13C NMR, 1H NMR, FT-IR and MS as well as by a single crystal X-ray structural analysis. Additionally, the structure of the single crystal was confirmed using X-ray diffraction. The packing of the molecules in the solid state is dominated by hydrogen bonds. The optimized structure of the compound was computed via DFT using the B3LYP functional with the 6-311G(2d, p) as basis set and compared with that determined using X-ray diffraction. The results show that the crystal structure confirmed using X-ray diffraction is consistent with the molecular structure optimized using DFT. In addition, the anti-proliferative activity of the title compound on A375 cells was studied, and the inhibition rate at a concentration of 5 μM was 12.89%. Furthermore, molecular docking was performed to analyze the binding mode of the title compound with PI3Kγ.
- Zhou, Zhixu,Liu, Ye,Ren, Qian,Yu, Dehou,Lu, Hongguang
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- SYNTHESIS, CRYSTAL STRUCTURE AND DFT STUDY OF NOVEL (2S,2′S,6R,6′R)-4,4′-(6-BROMOPYRIDO[2,3-d]PYRIMIDINE-2,4-DIYL)BIS(2,6-DIMETHYLMORPHOLINE)
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Abstract: (2S,2′S,6R,6′R)-4,4′-(6-Bromopyrido[2,3-d]pyrimidine-2,4-diyl)bis(2,6-dimethylmorpholine) is a novel organic intermediate having pyrido[2,3-d]pyrimidine. It is synthesized by four steps and confirmed by 1H and 13C NMR and FTIR spectroscopy and MS. Meanwhile, the single crystal of the title compound is subjected to the crystallographic analysis and the conformation determination. Moreover, density functional theory (DFT) is used to calculate the optimized structures of the molecule which are compared with the X-ray measurement. The result of the molecular structure optimized by DFT is consistent with the crystal structure determined by single crystal X-ray diffraction. Finally, in order to further investigate some physical properties of the title compound by the B3LYP/6-311G(2d,p) method, the molecular electrostatic potential and frontier molecular orbitals are calculated. The calculated and experimental data show that the title compound has good chemical stability and nucleophilic reactivity. Hirshfeld surface analyses can explain the atom pair contacts of the crystal and the quantitative analysis of intermolecular interactions is performed. [Figure not available: see fulltext.]
- Chen, D.-M.,Chen, Y.-M.,Liao, W.-K.,Wu, Q.-M.,Ye, W.-J.,Zhao, C.-S.,Zhou, Z.-X.
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p. 1501 - 1510
(2021/11/20)
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- PYRIDOPYRIMIDINES DERIVATIVES AS P2X3 INHIBITORS
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The present invention relates to compounds of formula I inhibiting P2X purinoceptor 3 (hereinafter P2X3 inhibitors); particularly the invention relates to compounds that are pyridopyrimidines derivatives, methods of preparing such compounds, ph
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Page/Page column 81-82
(2020/12/11)
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- Regioselective palladium-catalyzed Suzuki–Miyaura coupling reaction of 2,4,6-trihalogenopyrido[2,3-d]pyrimidines
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An effective, regioselective, and novel strategy to the access of 2,4,6-trisubstituted pyrido[2,3-d]pyrimidines is developed from the corresponding 2,4,6-trihalogenopyrido[2,3-d]pyrimidine through a Suzuki–Miyaura coupling reaction involving a novel regioselective halogen discrimination.
- Riadi, Yassine,Lazar, Sa?d,Guillaumet, Gérald
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p. 294 - 298
(2019/02/25)
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- Discovery and in vivo effects of novel human natriuretic peptide receptor A (NPR-A) agonists with improved activity for rat NPR-A
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Natriuretic peptide receptor A (NPR-A) agonists were evaluated in vivo by optimizing the structure of quinazoline derivatives to improve agonistic activity for rat NPR-A. A 1,4-Cis-aminocyclohexylurea moiety at 4-position and hydroxy group of D-alaninol at 2-position on the quinazoline ring were found to be important factors in improving rat NPR-A activity. We identified potent quinazoline and pyrido[2,3-d]pyrimidine derivatives against rat NPR-A, with double-digit nanomolar EC50 values. The in vivo results showed that compound 56b administered at 1.0 mg/kg/min significantly increased plasma cGMP concentration and urine volume in rats. We discovered novel potent NPR-A agonists that showed agonistic effects similar to those of atrial natriuretic peptide.
- Iwaki, Takehiko,Tanaka, Taisaku,Miyazaki, Kazuo,Suzuki, Yamato,Okamura, Yoshihiko,Yamaki, Akira,Iwanami, Makoto,Morozumi, Naomi,Furuya, Mayumi,Oyama, Yoshiaki
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p. 6680 - 6694
(2017/11/20)
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- HETEROCYCLIC COMPOUNDS, METHODS OF MAKING THEM AND THEIR USE IN THERAPY
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In part, the present invention is directed to antibacterial compounds of formula (I) wherein A is a bicyclic heteroaryl ring or a tricyclic ring and R2 is an heterocyclic residue; L is a bond, or L is alkyl, alkenyl or cycloalkyl.
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Page 56; 114
(2010/02/07)
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- PYRIMIDINES, XXXII: SYNTHESIS AND PROPERTIES OF PYRIDOPYRIMIDINE-2,4-DIONES (5-DEAZALUMAZINES)
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Pyridopyrimidine-2,4-dione (8) and its N-methyl derivatives (9-11) as well as the corresponding 6-nitro analogues (12-15) have been synthesized by condensation reactions from 6-aminouracils (4-7).Reduction of compound (4-7) led to the 6-aminopyrido
- Pfleiderer, Mathias,Pfleiderer, Wolfgang
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p. 905 - 929
(2007/10/02)
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