- Exploring boron applications in modern agriculture: A structure-activity relationship study of a novel series of multi-substitution benzoxaboroles for identification of potential fungicides
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Several boron-containing small molecules have been approved by the US FDA to treat human diseases. We explored potential applications of boron-containing compounds in modern agriculture by pursuing multiple research and development programs. Here, we report a novel series of multi-substitution benzoxaboroles (1–36), a compound class that we recently reported as targeting geranylgeranyl transferase I (GGTase I) and thereby inhibiting protein prenylation (Kim et al., 2020). These compounds were designed, synthesized, and tested against the agriculturally important fungal pathogens Mycosphaerella fijiensis and Colletotrichum sublineolum in a structure–activity relationship (SAR) study. Compounds 13, 28, 30, 34 and 36 were identified as active leads with excellent antifungal MIC95 values in the range of 1.56–3.13 ppm against M. fijiensis and 0.78–3.13 ppm against C. sublineolum.
- Liu, Chunliang,Steere, Luke,McGregor, Cari,Frederick, Brittany H.,Pastoor, Timothy,Zhou, Yasheen,Liu, C. Tony,Cai, Yan,Zhou, Haibo,Xu, Musheng,Wang, Jiangong,Kim, Sang Hu,Whitesell, Luke,Cowen, Leah E.,Zhang, Yong-Kang
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supporting information
(2021/05/19)
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- Benzoxaborole Catalyst for Site-Selective Modification of Polyols
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The site-selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site-selective and protecting-group-free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a–k were synthesized. In-depth analysis for the substituent effect revealed that 1i–k, bearing multiple electron-withdrawing fluoro- and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i-catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis-1,2-diol derivatives proceeded with good yield and site-selective manner.
- Kusano, Shuhei,Miyamoto, Shoto,Matsuoka, Aki,Yamada, Yuji,Ishikawa, Ryuta,Hayashida, Osamu
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supporting information
p. 1598 - 1602
(2020/02/11)
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- BORON CONTAINING COMPOUNDS AND THEIR USES
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The present disclosure contemplates novel boron-containing compounds and their uses as active agents that exhibit pesticidal activity such as antimicrobial, insecticidal, arachnicidal, and/or anti parasitic activity. An agrochemical composition containing such a compound and its use in, animal health, agriculture, or horticulture is also contemplated. A method for promoting plant performance and/or controlling, reducing, preventing, ameliorating, or inhibiting microbes, insects, arachnids, and/or parasites on or in an animal, a plant, a plant part, plant propagation material, and/or harvested fruits or vegetables is also contemplated.
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Paragraph 0224-0225
(2020/03/29)
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- An Efficient Benzoxaborole One-Pot Synthesis by SiliaCat DPP-Pd Heterogeneous Catalysis using Diboronic Acid
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Organoboron compounds are valuable molecules of increasing interest in organic synthesis, catalysis, biology and medicine. Among them, benzoxaboroles emerged as promising building blocks for numerous research programs. In this letter, we communicate the development of new conditions for the one-pot benzoxaborole synthesis by SiliaCat DPP?Pd catalysis using diboronic acid as the boron source. This low cost and sustainable strategy permitted the preparation of a useful range of benzoxaborole building blocks. Finally, the transformation was extended to a continuous flow process using our Vapourtec system. (Figure presented.).
- Kunihiro, Kana,Dumais, Laurence,Lafitte, Guillaume,Varvier, Emeric,Tomas, Lo?c,Harris, Craig S.
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supporting information
p. 2757 - 2761
(2018/06/04)
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- Preparation method of 3,3-dimethylbenz[C][1,2]oxa-pentaborane-1(3H)-alcohol
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The invention relates to a preparation method of 3,3-dimethylbenz[C][1,2]oxa-pentaborane-1(3H)-alcohol. The preparation method comprises the following steps: mixing 2-phenyl-2-propyl alcohol and n-butyllithium in n-heptane under the condition of 0-10 DEG C, implementing hydroxyl lithiation, then raising the temperature to 40-60 DEG C to conduct lithiation on an ortho carbon atom; borating; addingsilver carbonate to have a decomposition reaction, extracting and washing an aqueous phase with alkali after acidifying hydrolysis, obtaining a sodium salt dispersing phase of the 3,3-dimethylbenz[C][1,2]oxa-pentaborane-1(3H)-alcohol; acidifying, extracting with a solvent, conducting vacuum concentration to obtain the 3,3-dimethylbenz[C][1,2]oxa-pentaborane-1(3H)-alcohol. The invention provides the method for preparing the 3,3-dimethylbenz[C][1,2]oxa-pentaborane-1(3H)-alcohol by using 2-phenyl-2-propyl alcohol as the raw material, the method chooses the proper lithiation temperature (0-10 DEGC) to obtain a target product, but the problem of the byproduct is serious at the same time, the proper post-processing method is chosen, the byproduct is reacted to become a target object after beingacidified, and therefore, the yield and the purity of the target object are increased.
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Paragraph 0057-0062; 0068; 0071; 0074; 0080; 0084; 0094
(2019/01/08)
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- A convenient one-pot synthesis of boroxoles from diboronic acid
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The preparation of the boroxole motif traditionally relies on a 3-step process and the use of n-butyl lithium that can limit substrate scope. Herein during our exploration toward novel RORγ inhibitors, we identified a convenient one-pot preparation of the motif in good yields with good substrate scope.
- Lafitte, Guillaume,Kunihiro, Kana,Bonneaud, Céline,Dréan, Bénédicte,Gaigne, Frédéric,Parnet, Véronique,Pierre, Romain,Raffin, Catherine,Vatinel, Rodolphe,Fournier, Jean-Fran?ois,Musicki, Branislav,Ouvry, Gilles,Bouix-Peter, Claire,Tomas, Loic,Harris, Craig S.
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supporting information
p. 3757 - 3759
(2017/09/12)
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- Synthesis of substituted benzooxaborinin-1-ols via palladium-catalysed cyclisation of alkenyl- and alkynyl-boronic acids
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Two new palladium-catalysed reactions have been developed for the synthesis of stable 4-substituted benzooxaborinin-1-ols. A palladium-catalysed cyclisation of ortho-alkenylbenzene boronic acids can be used to access 4-chlorobenzooxaborinin-1-ols via a Wa
- Benhamou, Laure,Walker, Daniel W.,Bu?ar, Dejan-Kre?imir,Aliev, Abil E.,Sheppard, Tom D.
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p. 8039 - 8043
(2016/09/09)
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- Synthesis of Mavatrep: A Potent Antagonist of Transient Receptor Potential Vanilloid-1
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The process development of Mavatrep (1), a potent transient receptor potential vanilloid-1 (TRPV1) antagonist, is described. The two key synthetic transformations are the synthesis of (E)-6-bromo-2-(4-(trifluoromethyl)styryl)1H-benzo[d]imidazole (4) and the Suzuki coupling of 4 with 3,3-dimethyl-3H-benzo[c][1,2]oxaborol-1-ol (5). Compound 1a was prepared in four chemical steps in 63% overall yield.
- Wells, Kenneth M.,Mehrman, Steven J.,Abdel-Magid, Ahmed F.,Ferraro, Caterina,Scott, Lorraine,Zhong, Hua Marlon,Teleha, Christopher A.,Ballentine, Scott,Li, Xun,Russell, Ronald K.,Spink, Jan M.,Diamond, Craig,Youells, Scott,Zhang, Yongzheng,Tsay, Fuh-Rong,Cesco-Cancia, Sergio,Manzo, Stephen M.,Beauchamp, Derek A.
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p. 1774 - 1783
(2015/12/01)
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- Ring structure and aromatic substituent effects on the p K a of the benzoxaborole pharmacophore
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In this work, we present an investigation into the physical properties of a unique class of aromatic boronic acids, the benzoxaboroles. Using spectrophotometric methods, the ionization constants of a family of substituted benzoxaboroles are determined. He
- Tomsho, John W.,Pal, Arnab,Hall, Dennis G.,Benkovic, Stephen J.
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supporting information; experimental part
p. 48 - 52
(2012/04/10)
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- BORON CONTAINING POLYBASIC BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTICS USES THEREOF
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Disclosed herein are polybasic bacterial efflux pump inhibitors containing boronic acid functionality and theft methods of synthesis, methods of use, and pharmaceutical compositions. Some embodiments include methods of treating or preventing a bacterial infection by co-administering to a subject infected with bacteria or at risk of infection with bacteria the efflux pump inhibitor with another anti-bacterial agent
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- Synthesis and SAR of acyclic HCV NS3 protease inhibitors with novel P4-benzoxaborole moieties
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We have synthesized and evaluated a new series of acyclic P4-benzoxaborole-based HCV NS3 protease inhibitors. Structure-activity relationships were investigated, leading to the identification of compounds 5g and 17 with low nanomolar potency in the enzymatic and cell-based replicon assay. The linker-truncated compound 5j was found to exhibit improved absorption and oral bioavailability in rats, suggesting that further reduction of molecular weight and polar surface area could result in improved drug-like properties of this novel series.
- Li, Xianfeng,Zhang, Suoming,Zhang, Yong-Kang,Liu, Yang,Ding, Charles Z.,Zhou, Yasheen,Plattner, Jacob J.,Baker, Stephen J.,Bu, Wei,Liu, Liang,Kazmierski, Wieslaw M.,Duan, Maosheng,Grimes, Richard M.,Wright, Lois L.,Smith, Gary K.,Jarvest, Richard L.,Ji, Jing-Jing,Cooper, Joel P.,Tallant, Matthew D.,Crosby, Renae M.,Creech, Katrina,Ni, Zhi-Jie,Zou, Wuxin,Wright, Jon
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supporting information; experimental part
p. 2048 - 2054
(2011/04/24)
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- BORON-CONTAINING SMALL MOLECULES AS ANTIPROTOZOAL AGENTS
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This invention provides, among other things, novel compounds useful for treating protozoal infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective agent. The compounds are of the following formula: wherein R1 is a member selected from alkyl or aryl or heteroaryl, in which at least one substituent on said alkyl or said aryl or said heteroaryl is optionally substituted with a member selected from halogen, C1 or C2 or C3 or C4 or C5 or C6 unsubstituted alkyl, C1 or C2 or C3or C4 or C5 or C6 unsubstituted alkoxy, halosubstituted C1 or C2 or C3or C4 or C5 or C6 alkyl, halosubstituted C1 or C2 or C3 or C4 or C5 or C6 alkoxy, unsubstituted C1 or C2 or C3 or C4or C5 or C6 alkylthio, unsubstituted phenyl; and X is aryl or heteroaryl, in which one substituent on said aryl or said heteroaryl is a member selected from halogen, unsubstituted C1 or C2 or C3 or C4 or C5 or C6 alkyl, unsubstituted C1 or C2 or C3 or C4 or C5 or C6 alkoxy, halosubstituted C1 or C2 or C3 or C4 or C5 or C6 alkyl, halosubstituted C1 or C2 or C3 or C4 or C5 or C6 alkoxy, unsubstituted C1 or C2 or C3 or C4 or C5 or C6 alkylthio, unsubstituted phenyl or a salt thereof.
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Page/Page column 103-104
(2011/02/24)
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- BORON-CONTAINING SMALL MOLECULES AS ANTIPROTOZOAL AGENTS
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This invention provides, among other things, novel compounds useful for treating protozoal infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective
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Page/Page column 135-136
(2011/02/24)
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- BENZIMIDAZOLE TRPV1 INHIBITORS
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The invention is directed to compounds of Formula (I): to pharmaceutical compositions containing such compounds and to methods of treatment using them.
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Page/Page column 44
(2008/12/06)
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- Benzimidazole Modulators of VR1
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The invention is directed to compounds of Formula (I): to pharmaceutical compositions containing such compounds and to methods of treatment using them.
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Page/Page column 168
(2008/06/13)
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- Synthesis and structure of benzoboroxoles: Novel organoboron heterocycles
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Benzoboroxoles (5) can be prepared from the readily available o-bromobenzyl alcohols via dilithiation followed by reaction with triisopropylborate. X-Ray structural analysis of 1-hydroxy-3(1H)-1,2-benzoboroxole (5a) as well as the results of ab initio molecular orbital calculations indicate a planar structure of the boron center with a relatively short C-B bond. Preliminary results regarding the chemistry of benzoboroxoles are also reported.
- Zhdankin, Viktor V.,Persichini III,Zhang, Lu,Fix, Shannon,Kiprof, Paul
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p. 6705 - 6708
(2007/10/03)
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