Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas

Zhou, Yu; Wang, Jiang; Gu, Zhe‐Ming; Wang, Shuni; Zhu, Wei; Aceña, José Luis; Soloshonok, Vadim A.; Izawa, Kunisuke; Liu, Hong

doi:10.1021/acs.chemrev.5b00392

Cited by 2,298 publications

(1,212 citation statements)

References 594 publications

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“…Organofluorine affects nearly all physical and adsorption, distribution, metabolism, and excretion properties of a lead compound. Its inductive effects are relatively well understood and enhancing bioavailability [25][26][27]. Top-selling fluorinated pharmaceuticals include the antidepressant fluoxetine (Prozac), the cholesterol-lowering drug atorvastatin (Lipitor), and the antibacterial ciprofloxacin (Ciprobay) (Figure 2) [28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-Tumor Activities of Fluoride-Containing Gossypol Derivatives Compounds

Zeng¹,

Deng²,

Weng³

et al. 2017

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We report herein the design and synthesis of a series of novel fluoride-containing gossypol derivatives by the condensation reaction of gossypol with fluoride-containing aromatic amine. These fluoride-containing gossypol derivatives were characterized by IR, 1 H-NMR and high resolution mass spectral data, then screened as antitumor agents against three human cancer cell lines (HeLa, A-549 and BGC-823) and a normal cell line (VEC) in vitro by using MTT cell proliferation assays. Results revealed that compounds 3a, 3c and 3f exhibited superior anticancer activity against HeLa, compounds 3b,3c, 3e and 3f exhibited superior anticancer activity against A-549, compounds 3b, 3c and 3f exhibited superior anticancer activity against BGC-823 compared to gossypol. In particular, fluorine substituent at the para positions of the phenyl ring showed remarkable inhibitory effects on HeLa (3c: IC 50 = 14.2 μM, 3f: IC 50 = 8.34 μM), A-549(3c: IC 50 = 6.32 μM, 3f: IC 50 = 9.76 μM) and BGC-823 cells (3c: IC 50 = 8.62 μM, 3f: IC 50 = 4.36 μM). Furthermore, all the compounds 3a-3f exhibited lessened cytotoxicity against VEC compared to gossypol.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-Tumor Activities of Fluoride-Containing Gossypol Derivatives Compounds

Zeng¹,

Deng²,

Weng³

et al. 2017

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“…Because of the high importance of fluorinated biomolecules in drug design, the introduction of one or more fluorine atoms into an organic molecule has attracted high interest over the past ten years [6][7][8][9][10]. In view of the significance of a fluorine atom in an organic molecule, epoxide opening with fluoride, without doubt, is a highly useful approach for the introduction of a fluorine atom into a certain molecule [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Fluorination of some functionalized cycloalkenes through epoxidation and oxirane opening with Deoxofluor or XtalFluor-E

Remete¹,

Fülöp²,

Kiss³

2017

FLUOR. NOTES

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“…Fluorinated derivatives of pyridines are of high significance in pharmaceutical and medicinal chemistry [11]. Synthesis of poly substituted fluroarylazopyridone by using green protocol is of great effect in synthetic chemistry and also in pharmaceutical chemistry [12].…”

Section: Introductionmentioning

confidence: 99%

“…Genetic mutation and acquisition of mobile drug resistance genes of microorganisms is a very great resistance and barrier in treating animal and human patients with infectious diseases [4,5]. The importance of the synthesis of novel derivatives of pyridine nucleosides due to their potential use to treat various diseases, such as hepatitis cancer and microbial infections [6][7][8][9][10].Fluorinated derivatives of pyridines are of high significance in pharmaceutical and medicinal chemistry [11]. Synthesis of poly substituted fluroarylazopyridone by using green protocol is of great effect in synthetic chemistry and also in pharmaceutical chemistry [12].…”

mentioning

confidence: 99%

Green Synthesis of Novel 5-Arylazo-2- [(2S, 3S, 4R, 5R)-3, 4, 5- trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4, 6-dimethyl 3-nicotinonitrile.

Mmh¹,

Ah²,

M³

et al. 2017

Chem Sci J

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Green Synthesis of Novel 5-Arylazo-2-[(2S, 3S, 4R, 5R)-3, 4, 5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4, 6-dimethyl 3-nicotinonitrile IntroductionPyridine nucleus is one of the most interesting nucleus in organic synthesis. Many uses of pyridines derivatives were investigated in the recent decades especially fluorinated derivatives. One of the recent researches discovered that high tuberculostearic activity of pyridine was observed [1,2].Also from the amazing character of some pyridine is its high fluorescence activities which was used as molecular sensor of picric acid [3].It has been of great importance in the exploring of some novel antimicrobial compounds in veterinary as well as human medicine worldwide. Genetic mutation and acquisition of mobile drug resistance genes of microorganisms is a very great resistance and barrier in treating animal and human patients with infectious diseases [4,5]. The importance of the synthesis of novel derivatives of pyridine nucleosides due to their potential use to treat various diseases, such as hepatitis cancer and microbial infections [6][7][8][9][10].Fluorinated derivatives of pyridines are of high significance in pharmaceutical and medicinal chemistry [11]. Synthesis of poly substituted fluroarylazopyridone by using green protocol is of great effect in synthetic chemistry and also in pharmaceutical chemistry [12]. The presence of fluorine atoms in the molecule can change its lipophilicity, which also affect and change the rate of transportation through lipid membranes [13]. Achievement of green and sustainable chemistry protocol instead of classical methods synthetic chemistry nowadays is of high interest, especially in synthesis of some novel Fluro arylazo pyridine derivatives (1a-e) and their nucleosides (3a-e). Methodology ChemistryGeneral coupling procedures of synthesis of Acetylated -arylazo-2-[(2S, 3S, 4R, 5R)-3, 4, 5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4,6dimethylnicotinonitrile AbstractPyridine derivatives played important roles in the last decade in to approach many and different functionalities, especially as antitumor, antibacterial, anti-fungal, and many of pharmacological activities. Novel compounds of 5-Arylazo-2-[(substituted)-3,4,5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4,6dimethyl nicotine nitrile, (3a-e), generally called (Fluro arylazo pyridine glucosides) were synthesised via green protocol, microwave scheme 3, and the compounds were investigated on the basis of spectroscopic data (FT-IR, 1D, 13 C), and antibacterial and antifungal studies had been applied. Microwave method: A mixture of 2(1H)-pyridines (1a-e) (10 mmol) and 1″,2″,3″,4″,6″-penta-O-acetyl-α-D-glucopyranose (11 mmol, 4.29 g) where be dissolved in a mixture of methylene chloride/methanol (80/20) then silica gel (200-400 mesh) where be added after that the excess solvent was removed by evaporation. The dried residue was transferred into a 10 mL vial and subjected to microwave irradiation for 2-3 minutes using CEM Microwave syst...

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Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II–III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas

Cited by 2,298 publications

References 594 publications

Synthesis and Anti-Tumor Activities of Fluoride-Containing Gossypol Derivatives Compounds

Synthesis and Anti-Tumor Activities of Fluoride-Containing Gossypol Derivatives Compounds

Fluorination of some functionalized cycloalkenes through epoxidation and oxirane opening with Deoxofluor or XtalFluor-E

Green Synthesis of Novel 5-Arylazo-2- [(2S, 3S, 4R, 5R)-3, 4, 5- trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4, 6-dimethyl 3-nicotinonitrile.

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