{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,21]],"date-time":"2026-10-21T15:55:21Z","timestamp":1792598121379,"version":"4.5.0"},"reference-count":63,"publisher":"American Chemical Society (ACS)","issue":"41","license":[{"start":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T00:00:00Z","timestamp":1791331200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T00:00:00Z","timestamp":1791331200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T00:00:00Z","timestamp":1791331200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100013200","name":"Government of Alberta","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100013200","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000038","name":"Natural Sciences and Engineering Research Council of Canada","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100000038","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,21]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The advent of benzoxaborole drugs brought attention to hemiboronic heterocycles as an attractive chemotype, where they can be implicated in a number of biological contexts. However, the success of benzoxaboroles, a neutral-pKa scaffold, has yet to be replicated with other classes of boranol (B\u2013OH)-containing heterocycles. Although six-membered borine homologs may exist with various permutations of endocyclic heteroatoms and functional groups, little is known about structure-property relationships. Here, a systematic study of more than 15 non-aromatic and pseudo-aromatic hemiboronic benzoborines derived from ortho-substituted arylboronic acids was achieved, using pKa as a guiding principle, to identify scaffolds that emulate benzoxaboroles. A wide range of pKa\u2019s were observed across all scaffolds, with one neutral-pKa scaffold, borylurea, found to possess stability, lipophilicity, and other attributes similarly favorable to those of benzoxaborole. The borylurea scaffold embeds more heteroatoms to engage in molecular interactions with target proteins, it presents promising DMPK characteristics, and it is readily amenable to chemical diversification. NMR studies confirmed that it reacts to form complexes with small biomolecules like monosaccharides and ribonucleosides with an efficiency superior to that of benzoxaborole in organic medium, and comparable in aqueous conditions. Altogether, this study underscores the considerable advantage of properties, reactivity, and convenience offered by neutral-pKa boroheterocycles.<\/jats:p>","DOI":"10.1021\/jacs.6c17387","type":"journal-article","created":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T04:01:41Z","timestamp":1791432101000},"page":"45167-45183","source":"Crossref","is-referenced-by-count":0,"title":["Benzoxaborole-Inspired\np\n                    <i>K<\/i>\n                    a-Guided Search for a Borine\nAlternative Uncovers a Borylurea\nScaffold with Unique Properties and Reactivity"],"prefix":"10.1021","volume":"148","author":[{"given":"Olivia M.","family":"Schneider","sequence":"first","affiliation":[{"name":"University of Alberta , , , ,","place":["Edmonton, Alberta, Canada, T6G 2G2"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-5279-4515","authenticated-orcid":true,"given":"Jake J.","family":"Blackner","sequence":"additional","affiliation":[{"name":"University of Alberta , , , ,","place":["Edmonton, Alberta, Canada, T6G 2G2"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joana","family":"Sugiarto","sequence":"additional","affiliation":[{"name":"University of Alberta , , , ,","place":["Edmonton, Alberta, Canada, T6G 2G2"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ridge Michael P.","family":"Ylagan","sequence":"additional","affiliation":[{"name":"University of Alberta , , , ,","place":["Edmonton, Alberta, Canada, T6G 2G2"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marco","family":"Paladino","sequence":"additional","affiliation":[{"name":"University of Alberta , , , ,","place":["Edmonton, Alberta, Canada, T6G 2G2"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michele","family":"Boghi","sequence":"additional","affiliation":[{"name":"University of Alberta , , , ,","place":["Edmonton, Alberta, Canada, T6G 2G2"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-8303-1198","authenticated-orcid":true,"given":"Kathryn","family":"Robinson","sequence":"additional","affiliation":[{"name":"University of Alberta , , , ,","place":["Edmonton, Alberta, Canada, T6G 2G2"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7273-2302","authenticated-orcid":true,"given":"Dawson J.","family":"Konowalchuk","sequence":"additional","affiliation":[{"name":"University of Alberta , , , ,","place":["Edmonton, Alberta, Canada, T6G 2G2"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0007-8539-4158","authenticated-orcid":true,"given":"Matthew","family":"Sutherland","sequence":"additional","affiliation":[{"name":"University of Alberta , , , ,","place":["Edmonton, Alberta, Canada, T6G 2G2"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Keaton","family":"Mah","sequence":"additional","affiliation":[{"name":"University of Alberta , , , ,","place":["Edmonton, Alberta, Canada, T6G 2G2"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8555-6400","authenticated-orcid":true,"given":"Dennis G.","family":"Hall","sequence":"additional","affiliation":[{"name":"University of Alberta , , , ,","place":["Edmonton, Alberta, Canada, T6G 2G2"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,7]]},"reference":[{"key":"2026102111100132500_cit1","doi-asserted-by":"publisher","first-page":"100075","DOI":"10.1016\/j.medidd.2020.100075","article-title":"Biologics\nvs. Small Molecules: Drug cost and patient access","volume":"9","author":"Makurvet","year":"2021","journal-title":"Med. Drug Discovery"},{"key":"2026102111100132500_cit2","doi-asserted-by":"publisher","first-page":"8408","DOI":"10.1021\/acs.jmedchem.0c00754","article-title":"The Most Common\nFunctional Groups\nin Bioactive Molecules and How Their Popularity Has Evolved over Time","volume":"63","author":"Ertl","year":"2020","journal-title":"J. Med. Chem."},{"key":"2026102111100132500_cit3","doi-asserted-by":"publisher","first-page":"10170","DOI":"10.1021\/acs.jmedchem.0c00415","article-title":"Essential\nMedicinal Chemistry of Essential Medicines","volume":"63","author":"Serafini","year":"2020","journal-title":"J. Med. Chem."},{"key":"2026102111100132500_cit4","doi-asserted-by":"publisher","first-page":"6405","DOI":"10.1021\/jm200504p","article-title":"What Do\nMedicinal\nChemists Actually Make? A 50-Year Retrospective","volume":"54","author":"Walters","year":"2011","journal-title":"J. Med. Chem."},{"key":"2026102111100132500_cit5","doi-asserted-by":"publisher","first-page":"2114","DOI":"10.1021\/acsmedchemlett.0c00319","article-title":"Structural Approach to Assessing the Innovativeness\nof New Drugs Finds Accelerating Rate of Innovation","volume":"11","author":"Wills","year":"2020","journal-title":"ACS Med. Chem. Lett."},{"key":"2026102111100132500_cit6","doi-asserted-by":"publisher","first-page":"12697","DOI":"10.1021\/acs.jmedchem.3c01101","article-title":"Oxetanes in Drug\nDiscovery Campaigns","volume":"66","author":"Rojas","year":"2023","journal-title":"J. Med. Chem."},{"key":"2026102111100132500_cit7","doi-asserted-by":"publisher","first-page":"679","DOI":"10.1016\/j.ejmech.2018.11.017","article-title":"Pharmaceutical\nand medicinal significance of sulfur (SVI)-Containing motifs for drug\ndiscovery: A critical review","volume":"162","author":"Zhao","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"2026102111100132500_cit8","doi-asserted-by":"publisher","first-page":"14243","DOI":"10.1021\/acs.jmedchem.0c00960","article-title":"Sulfoximines as Rising\nStars in Modern Drug Discovery?\nCurrent Status and Perspective on an Emerging Functional Group in\nMedicinal Chemistry","volume":"63","author":"Ma\u0308der","year":"2020","journal-title":"J. Med. Chem."},{"key":"2026102111100132500_cit9","doi-asserted-by":"publisher","first-page":"11585","DOI":"10.1021\/acs.jmedchem.0c00746","article-title":"Nonclassical Phenyl Bioisosteres\nas Effective Replacements in a Series of Novel Open-Source Antimalarials","volume":"63","author":"Tse","year":"2020","journal-title":"J. Med. Chem."},{"key":"2026102111100132500_cit10","doi-asserted-by":"publisher","first-page":"1184","DOI":"10.1021\/jacs.7b09446","article-title":"The State of the Art in Azaborine\nChemistry: New Synthetic\nMethods and Applications","volume":"140","author":"Giustra","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111100132500_cit11","doi-asserted-by":"publisher","first-page":"791","DOI":"10.1016\/j.ejmech.2019.06.092","article-title":"Boron in\nDrug Design: Recent Advances in the Development of New Therapeutic\nAgents","volume":"179","author":"Santos Fernandes","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"2026102111100132500_cit12","doi-asserted-by":"publisher","first-page":"116748","DOI":"10.1016\/j.bmc.2022.116748","article-title":"Boron-Containing Heterocycles as\nPromising Pharmacological Agents","volume":"63","author":"Das","year":"2022","journal-title":"Bioorg. Med.\nChem."},{"key":"2026102111100132500_cit13","doi-asserted-by":"publisher","first-page":"2441","DOI":"10.1021\/acs.chemrev.3c00663","article-title":"The Rise of Boron-Containing\nCompounds: Advancements in Synthesis, Medicinal Chemistry, and Emerging\nPharmacology","volume":"124","author":"Grams","year":"2024","journal-title":"Chem. Rev."},{"key":"2026102111100132500_cit14","doi-asserted-by":"publisher","first-page":"1794","DOI":"10.1007\/s00044-016-1603-1","article-title":"Synthesis, Characterization,\nantimicrobial activity, and QSAR studies on substituted oxadiazaboroles","volume":"25","author":"Pir","year":"2016","journal-title":"Med. Chem. Res."},{"key":"2026102111100132500_cit15","doi-asserted-by":"publisher","first-page":"4849","DOI":"10.1039\/C8OB00998H","article-title":"Valdecoxib vs. borazavaldecoxib: isoxazole BN\/CC isosterism\nas a case study in designing and stabilizing boron heterocycles","volume":"16","author":"Boghi","year":"2018","journal-title":"Org. Biomol. Chem."},{"key":"2026102111100132500_cit16","doi-asserted-by":"publisher","first-page":"1321","DOI":"10.1016\/j.chembiol.2017.08.011","article-title":"Boron-Based Inhibitors of the NLRP3 Inflammasome","volume":"24","author":"Baldwin","year":"2017","journal-title":"Cell Chem. Biol."},{"issue":"23","key":"2026102111100132500_cit17","doi-asserted-by":"publisher","first-page":"9287","DOI":"10.1021\/acs.jmedchem.5b01088","article-title":"Benzazaborinines as Novel Bioisosteric Replacements\nof Naphthalene: Propranolol as an Example","volume":"58","author":"Rombouts","year":"2015","journal-title":"J.\nMed. Chem."},{"key":"2026102111100132500_cit18","doi-asserted-by":"publisher","first-page":"358","DOI":"10.1002\/cmdc.201700047","article-title":"Medicinal\nChemsitry Profiling of Monocyclic 1,2-Azaborines","volume":"12","author":"Zhao","year":"2017","journal-title":"ChemMedchem"},{"key":"2026102111100132500_cit19","doi-asserted-by":"publisher","first-page":"4994","DOI":"10.1039\/C8SC05167D","article-title":"Synthesis and Characterization of an Unnatural Boron and Nitrogen-containing\nTryptophan analogue and its Incorporation into Proteins","volume":"10","author":"Boknevitz","year":"2019","journal-title":"Chem. Sci."},{"key":"2026102111100132500_cit20","doi-asserted-by":"publisher","first-page":"5224","DOI":"10.1021\/cr500642d","article-title":"Recent Developments in the Chemistry\nand Biological Applications of Benzoxaboroles","volume":"115","author":"Adamczyk-Woz\u0301niak","year":"2015","journal-title":"Chem. Rev."},{"key":"2026102111100132500_cit21","doi-asserted-by":"publisher","first-page":"132057","DOI":"10.1016\/j.molstruc.2021.132057","article-title":"Benzoxaboroles: New emerging and\nversatile scaffold\nwith a plethora of pharmacological activities","volume":"1252","author":"Dhawan","year":"2022","journal-title":"J. Mol. Struct."},{"key":"2026102111100132500_cit22","doi-asserted-by":"publisher","first-page":"1241","DOI":"10.1080\/13543776.2025.2576513","article-title":"Therapeutic applications\nof benzoxaborole compounds: a patent and literature analysis (2019-2024)","volume":"35","author":"Giovannuzzi","year":"2025","journal-title":"Expert Opin. Ther. Pat."},{"key":"2026102111100132500_cit23","doi-asserted-by":"publisher","first-page":"4447","DOI":"10.1021\/jm0603724","article-title":"Discovery of a New Boron-Containing\nAntifungal Agent,\n5-Fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (AN2690), for the\nPotential Treatment of Onychomycosis","volume":"49","author":"Baker","year":"2006","journal-title":"J. Med.\nChem."},{"key":"2026102111100132500_cit24","doi-asserted-by":"publisher","first-page":"2129","DOI":"10.1016\/j.bmcl.2009.03.007","article-title":"Discovery and Structure-Activity\nStudy of a Novel Benzoxaborole Anti-Inflammatory Agent (AN2728) for\nthe Potential Topical Treatment of Psoriasis and Atopic Dermatitis","volume":"19","author":"Akama","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"2026102111100132500_cit25","doi-asserted-by":"publisher","first-page":"3682","DOI":"10.1021\/acs.jmedchem.5b00127","article-title":"Discovery of a Cyclic Boronic Acid\n\u03b2-Lactamase\nInhibitor (RPX7009) with Utility vs Class A Serine Carbapenemases","volume":"58","author":"Hecker","year":"2015","journal-title":"J. Med. Chem."},{"issue":"14","key":"2026102111100132500_cit26","doi-asserted-by":"publisher","first-page":"7491","DOI":"10.1021\/acs.jmedchem.9b01976","article-title":"Discovery of Cyclic\nBoronic Acid QPX7728, an Ultrabroad-Spectrum\nInhibitor of Serine and Metallo-\u03b2-lactamases","volume":"63","author":"Hecker","year":"2020","journal-title":"J. Med. Chem."},{"key":"2026102111100132500_cit27","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pntd.0001151","article-title":"SCYX-7158, an Orally-Active\nBenzoxaborole for\nthe Treatment of Stage 2 Human African Trypanosomiasis","volume":"5","author":"Jacobs","year":"2011","journal-title":"PLoS Negl. Trop. Dis."},{"key":"2026102111100132500_cit28","doi-asserted-by":"publisher","first-page":"1394","DOI":"10.1128\/AAC.02058-12","article-title":"Discovery\nof a Novel Class of Boron-based\nAntibacterials with Activity Against Gram-negative Bacteria","volume":"57","author":"Hernandez","year":"2013","journal-title":"Antimicrob. Agents Chemother."},{"key":"2026102111100132500_cit29","doi-asserted-by":"publisher","first-page":"8011","DOI":"10.1021\/acs.jmedchem.7b00631","article-title":"Discovery\nof a Potent and Specific\nM. tuberculosis Leucyl-tRNA Synthetase Inhibitor: (S)-3-(Aminomethyl)-4-chloro-7-(2-hydroxyethoxy)benzo[c]\n[1,2]oxaborol-1(3H)-ol (GSK656)","volume":"60","author":"Li","year":"2017","journal-title":"J. Med. Chem."},{"key":"2026102111100132500_cit30","doi-asserted-by":"publisher","first-page":"4","DOI":"10.1038\/d41591-022-00114-z","article-title":"A New Class\nof Antibiotics Delivers Promising Trial Results Against Tuberculosis","volume":"29","author":"Carvalho","year":"2023","journal-title":"Nat. Med."},{"key":"2026102111100132500_cit31","doi-asserted-by":"publisher","first-page":"19","DOI":"10.1111\/jvh.12753","article-title":"GSK2878175, a Pan-Genotypic Non-Nucleoside\nNS5B Polymerase Inhibitor, in Healthy and Treatment-Nai\u0308ve Chronic\nHepatitis C Subjects","volume":"25","author":"Gardner","year":"2018","journal-title":"J. Viral Hepatitis"},{"key":"2026102111100132500_cit32","doi-asserted-by":"publisher","first-page":"1534","DOI":"10.1021\/acs.chemrev.5c00703","article-title":"Benzoxaborole and\nBeyond: The Emergence of Cyclic Hemiboronic\nAcids as a Versatile Chemotype in Medicine, Catalysis, and Materials","volume":"126","author":"Blackner","year":"2026","journal-title":"Chem. Rev."},{"key":"2026102111100132500_cit33","doi-asserted-by":"publisher","first-page":"13768","DOI":"10.1021\/acs.jmedchem.3c01194","article-title":"Expanding the Role\nof Boron in New\nDrug Chemotypes: Properties, Chemistry, Pharmaceutical Potential of\nHemiboronic Naphthoids","volume":"66","author":"Kazmi","year":"2023","journal-title":"J. Med. Chem."},{"key":"2026102111100132500_cit34","doi-asserted-by":"publisher","first-page":"1097","DOI":"10.1021\/acsmedchemlett.6b00300","article-title":"Characterization\nof the Dynamic Equilibrium between Closed and Open Forms of the Benzoxaborole\nPharmacophore","volume":"7","author":"Vshyvenko","year":"2016","journal-title":"ACS Med. Chem. Lett."},{"key":"2026102111100132500_cit35","doi-asserted-by":"publisher","first-page":"6471","DOI":"10.1021\/jo800788s","article-title":"Benzoxaboroles as Efficient Glycopyranoside-Binding\nAgents in Physiological Conditions: Structure and Selectivity of Complex\nFormation","volume":"73","author":"Be\u0301rube\u0301","year":"2008","journal-title":"J. Org. Chem."},{"key":"2026102111100132500_cit36","doi-asserted-by":"publisher","first-page":"48","DOI":"10.1021\/ml200215j","article-title":"Ring Structure and Aromatic Substituent\nEffects on the pKa of the Benzoxaborole Pharmacophore","volume":"3","author":"Tomsho","year":"2012","journal-title":"ACS Med. Chem. Lett."},{"key":"2026102111100132500_cit37","doi-asserted-by":"publisher","first-page":"10143","DOI":"10.1021\/jacs.1c02462","article-title":"Lewis or Br\u00f8nsted? A Rectification\nof the Acidic and Aromatic Nature of Boranol-Containing Naphthoid\nHeterocycles","volume":"143","author":"Kazmi","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111100132500_cit38","doi-asserted-by":"publisher","first-page":"10570","DOI":"10.1021\/jacs.2c03429","article-title":"Unraveling the Silent Hydrolysis\nof Cyclic B\u2013X\/C\u2550C\nIsosteres: The Striking Impact of a Single Heteroatom on the Aromatic,\nAcidic, and Dynamic Properties of Hemiboronic Phenanthroids","volume":"144","author":"Ang","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111100132500_cit39","doi-asserted-by":"publisher","first-page":"19499","DOI":"10.1021\/jacs.4c06360","article-title":"Removing Neighboring\nRing Influence in Monocyclic B\u2013OH Diazaborines: Properties\nand Reactivity as Phenolic Bioisosteres with Dynamic Hydroxy Exchange","volume":"146","author":"Blackner","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111100132500_cit40","doi-asserted-by":"publisher","first-page":"6705","DOI":"10.1016\/S0040-4039(99)01303-9","article-title":"Synthesis and Structure of Benzoboroxoles: Novel Organoboron\nHeterocycles","volume":"40","author":"Zhdankin","year":"1999","journal-title":"Tetrahedron Lett."},{"issue":"34","key":"2026102111100132500_cit41","doi-asserted-by":"publisher","first-page":"6351","DOI":"10.1021\/acs.orglett.2c02722","article-title":"Boron-Assisted Selective\nCitrulline Modification under\nMild Conditions","volume":"24","author":"Zhao","year":"2022","journal-title":"Org. Lett."},{"key":"2026102111100132500_cit42","doi-asserted-by":"publisher","first-page":"S1","DOI":"10.1039\/p298700000s1","article-title":"Tables of Bond Lengths\ndetermined by X-Ray and Neutron\nDiffraction. Part 1. Bond Lengths in Organic Compounds","volume":"2","author":"Allen","year":"1987","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"2026102111100132500_cit43","doi-asserted-by":"publisher","first-page":"1660","DOI":"10.1021\/jo01258a027","article-title":"Preparation and reactions of o-(cyanomethyl)benzeneboronic\nacid","volume":"34","author":"Catlin","year":"1969","journal-title":"J. Org. Chem."},{"key":"2026102111100132500_cit44","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2013691118","article-title":"Boronic acid with\nhigh oxidative stability and utility in biological contexts","volume":"118","author":"Graham","year":"2021","journal-title":"Proc. Natl. Acad. Sci. U. S. A."},{"key":"2026102111100132500_cit45","doi-asserted-by":"publisher","first-page":"11667","DOI":"10.1021\/ja303181m","article-title":"Scope of\nthe Palladium-Catalyzed Aryl Borylation Utilizing Bis-Boronic Acid","volume":"134","author":"Molander","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111100132500_cit46","doi-asserted-by":"publisher","first-page":"3842","DOI":"10.1021\/cr030088+","article-title":"Nucleus-Independent\nChemical Shifts (NICS) as an Aromaticity Criterion","volume":"105","author":"Chen","year":"2005","journal-title":"Chem. Rev."},{"key":"2026102111100132500_cit47","doi-asserted-by":"publisher","first-page":"8039","DOI":"10.1039\/C6OB01419D","article-title":"Synthesis\nof substituted benzooxaborinin-1-ols via palladium-catalysed cyclisation\nof alkenyl- and alkynyl-boronic acids","volume":"14","author":"Benhamou","year":"2016","journal-title":"Org.\nBiomol. Chem."},{"issue":"2","key":"2026102111100132500_cit48","doi-asserted-by":"publisher","first-page":"183","DOI":"10.1107\/S0108270113000681","article-title":"1-Hydroxy-1H-benzo[d][1,2,6]oxazaborinin-4(3H)-one","volume":"69","author":"Sarina","year":"2013","journal-title":"Acta Crystallogr., Sect C: cryst. Struct. Commun."},{"key":"2026102111100132500_cit49","doi-asserted-by":"publisher","first-page":"7597","DOI":"10.1021\/ja00096a017","article-title":"Boron Heterocycles\nBearing a Peripheral\nResemblance to Naturally-Occuring Purines: Design, Syntheses, Structures,\nand Properties","volume":"116","author":"Groziak","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111100132500_cit50","doi-asserted-by":"publisher","first-page":"4492","DOI":"10.1021\/jo9702249","article-title":"Enhanced Carboxylate\nBinding Using Urea and Amide-Based\nReceptors with Internal Lewis Acid Coordination: A Cooperative Polarization\nEffect","volume":"62","author":"Hughes","year":"1997","journal-title":"J. Org. 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Am. Chem. Soc."},{"key":"2026102111100132500_cit54","doi-asserted-by":"publisher","first-page":"3","DOI":"10.1016\/S0169-409X(00)00129-0","article-title":"Experimental and\ncomputational approaches to estimate solubility and permeability in\ndrug discovery and development settings","volume":"46","author":"Lipinski","year":"2001","journal-title":"Adv.\nDrug Delivery Rev."},{"key":"2026102111100132500_cit55","doi-asserted-by":"publisher","first-page":"55","DOI":"10.1021\/cc9800071","article-title":"A Knowledge-Based\nApproach in Designing\nCombinatorial or Medicinal Chemistry Libraries for Drug Discovery.\n1. A Qualitative and Quantitative Characterization of Known Drug Databases","volume":"1","author":"Ghose","year":"1999","journal-title":"J. Comb. Chem."},{"key":"2026102111100132500_cit56","unstructured":"Baker, S. J.; Akama, T.; Hernandez, V. S.; Hold, K. M.; Leyden, J. J.; Maples, K. R.; Plattner, J. J.; Sanders, V.; Zhang, Y.K.\n          Boron-Containing Small Molecules. 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