- Sulfonamides as Amine Component in the Petasis-Borono Mannich Reaction: A Concise Synthesis of α-Aryl- and α-Alkenylglycine Derivatives
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A catalyst-free three-component synthesis of α-aryl- and α-alkenylglycine derivatives starting from glyoxylic acid, sulfonamides, and aryl- or alkenylboronic acids is described. This operationally simple method tolerates a broad range of functional groups and enables the generation of a wide array of α-amino acids. Sulfonamides were utilized as amine component in the classic Petasis reaction for the first time.
- Diehl, Andreas M.,Ouadoudi, Omar,Andreadou, Eleni,Manolikakes, Georg
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p. 3936 - 3946
(2018/07/30)
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- Pd(ii)-Catalyzed aerobic 1,2-difunctionalization of conjugated dienes: Efficient synthesis of morpholines and 2-morpholones
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A novel and efficient methodology concerning the Pd(ii)-catalyzed intermolecular difunctionalization of conjugated dienes is reported to synthesize a series of functionalized morpholines and 2-morpholones. Widely distributed and easily obtained β-amino alcohols and α-amino acids, as starting nitrogen and oxygen sources, are successfully applied in the difunctionalization of conjugated dienes respectively. The majority of the desired products were obtained in moderate to excellent yields. Oxygen was successfully employed as a terminal oxidant. Further transformation of the generated products allowed for the expansion of structural diversity.
- Wen, Ke,Wu, Zhengxing,Chen, Buyun,Chen, Jianzhong,Zhang, Wanbin
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supporting information
p. 5618 - 5625
(2018/08/17)
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- Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors
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Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COL_G and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group. The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34 μM, 29.61 μM, 28.39 μM, 31.4 and 32.11 μM respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02 μM showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results.
- Ganeshpurkar, Ankit,Kumar, Devendra,Singh, Sushil Kumar
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p. 1491 - 1500
(2017/10/23)
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- One-step synthesis of racemic α-amino acids from aldehydes, amine components, and gaseous CO2 by the aid of a bismetal reagent
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α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid can be divided into three basic components: an aldehyde, an amine, and carbon dioxide (CO2). We report herein that a one-step synthesis of α-amino acids has been successfully achieved from these three basic and inexpensive chemicals with a single operation, in which the mixture of an aldehyde, a sulfonamide, and gaseous CO2 was heated at 100 °C in the presence of Bu3Sn-SnBu3 and CsF. In this one-pot sequential protocol, two important intermediates (imine and α-amino stannane) are involved and the stannyl anion generated in situ plays a crucial role, particularly for the efficient stannylation of the imine in the presence of proton sources and for promoting retrostannylation of the undesired α-alkoxy stannane owing to its high stability and tolerance of the presence of proton sources. This methodology enabled the synthesis of a wide range of racemic arylglycine derivatives in high yields. Go retro! α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid is retrosynthesized to an aldehyde, an amine, and carbon dioxide. A one-step synthesis of α-amin Copyright
- Mita, Tsuyoshi,Higuchi, Yuki,Sato, Yoshihiro
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p. 1123 - 1128
(2013/02/23)
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- Aminoacids in the synthesis of heterocyclic systems: The synthesis of triazinoquinazolinones, triazepinoquinazolinones and triazocinoquinazolinones of potential biological interest
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A number of novel triazinoquinazolinones (5b,c and 8), triazepinoquinazolinones(5a, 6b, 7 and 9) and triazocinoquinazolinones (6a and 10) were obtained via nucleophilic interaction of 3-aminoquinazolinone derivatives 3 with different reagents.
- El-Sharief,Ammar,Zahran,Ali,El-Gaby
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p. 267 - 278
(2007/10/03)
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- Preparation of a 3-phenyl-4(3H)-isoquinolinone and its transformation in 12(11H)-benzo[c]phenanthridinone derivatives. Crystal structure determinations
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Trans- and cis-5-(p-toluenesulfonyl)-5,6,13,14-tetrahydro-12(11H)-benzo[c]phanant hridinones have been prepared with excellent yield involving the initial formation of 3-phenyl-2-(p-toluenesulfonyl)-1,2-dihydro-4(3H)-isoquinolinone, as the key intermediat
- Gonzalez-Cameno, Ana M.,Badia, Dolores,Dominguez, Esther,Urtiaga, M. Karmele,Arriortua, M. Isabel,Solans, Xavier
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p. 10971 - 10982
(2007/10/02)
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