- Preparation method of o-nitrile phenylboronic acid-1, 3-propylene glycol ester
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The invention discloses a preparation method of o-nitrile phenylboronic acid-1, 3-propylene glycol ester, which belongs to the technical field of organic boric acid chemistry. The method comprises thefollowing steps of starting from o-bromobenzonitrile, carrying out a one-pot reaction with borate/n-butyllithium or metal lithium/boron halide amine, after the reaction is detected to be finished, carrying out acidolysis to obtain 2-nitrile phenylboronic acid, or directly filtering, distilling, adding 1, 3-propylene glycol to form ester, pulping, and purifying to obtain the o-nitrile phenylboronic acid-1, 3-propylene glycol ester. The key point of the process is that the reaction liquid is added into the acid water for quenching after the reaction is finished, so that the condition that the acid water is added into a reaction system to be subjected to an alkaline environment first and then to an acid environment is avoided, the yield is kept stable in different amplification stages, and the process has an industrial amplification prospect. And corresponding boric acid ester can be smoothly obtained by replacing propylene glycol with other glycols.
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Paragraph 0032-0035
(2021/01/29)
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- The discovery of new potent non-peptide Angiotensin II AT1 receptor blockers: A concise synthesis, molecular docking studies and biological evaluation of N-substituted 5-butylimidazole derivatives
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A convenient and facile synthesis, in silico docking studies and in vitro biological evaluation of N-substituted 5-butylimidazole derivatives as potent Angiotensin II (ANG II) receptor type 1 (AT1) blockers (ARBs) has been reported in the current study. Our efforts have been directed towards the development of an efficient synthetic route allowing the facile introduction of substituents on the imidazole ring. In particular, a series of imidazole based compounds bearing the biphenyl moiety at the N - 1 position, a halogen atom at the C-4 and polar substituents such as hydroxymethyl, aldo or carboxy group at the C-2 position were designed and synthesized. These compounds were evaluated for binding to human AT1 receptor and for ANG II antagonism in vitro on isolated rat uterus. Among them, 5-butyl-1-[[2′-(2H-tetrazol-5-yl)biphenyl-4-yl] methyl]imidazole-2-carboxylic acid (30) exhibited higher binding affinity compared to the other analogues tested (-log IC50 = 8.46). The latter analogue was also found to be the most active in the rat uterotonic test (pA2 = 7.83). Importantly, the binding affinity was higher to that of losartan (-log IC50 = 8.25) indicating the importance of carboxy group at the C-2 position. Experimental findings are in good agreement with docking studies, which were undertaken in order to investigate ligand/AT1 receptor interactions.
- Agelis, George,Resvani, Amalia,Matsoukas, John,Durdagi, Serdar,Spyridaki, Katerina,Liapakis, George,Tumova, Tereza,Slaninova, Jirina,Giannopoulos, Panagiotis,Mavromoustakos, Thomas,Vlahakos, Demetrios
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p. 358 - 374,17
(2020/07/30)
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- An efficient synthesis of sterically hindered arylboronic acids
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Boronic acids are important intermediates and molecular recognition moieties in a wide variety of applications. In our research, we have found that the synthesis of ortho-substituted arylboronic acids is problematic with the commonly used bis(pinacolato)diboron in palladium-mediated borylation reactions. As a substitute, we have found that bis(neopentyl glycolato)diboron is a much more efficient borylation agent for the synthesis of sterically hindered ortho-substituted arylboronic acids.
- Fang, Hao,Kaur, Gurpreet,Yan, Jun,Wang, Binghe
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p. 1671 - 1674
(2007/10/03)
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- Synthesis of Ortho Substituted Arylboronic Esters by in Situ Trapping of Unstable Lithio Intermediates
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matrix presented Ortho lithiation-in situ boration using lithium 2,2,6,6-tetramethylpiperidide (LTMP) in combination with triisopropylborate (B(OiPr)3) is a highly efficient and experimentally straightforward process for the preparation of ortho substituted arylboronic esters. The mild reaction conditions allow the presence of functionalities such as ester or cyano groups or halogen substituents that are usually not compatible with the conditions used in directed ortho metalation of arenes. The arylboronic esters underwent Suzuki-type cross-coupling with a range of aryl halides, furnishing biaryls in 53-94% yield.
- Kristensen, Jesper,Lysen, Morten,Vedso, Per,Begtrup, Mikael
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p. 1435 - 1437
(2007/10/03)
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