- Electro-Oxidative Selective Esterification of Methylarenes and Benzaldehydes
-
A mild and green electro-oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro-oxidative coupling process also displays exceptional tolerance of many fragile easily oxidized functional groups such as hydroxy, aldehyde, olefin, alkyne, as well as neighboring benzylic positions. The enantiomeric enrichment of some chiral alcohols is moreover preserved during this electro-oxidative coupling reaction, making it overall a promising synthetic tool.
- Yu, Congjun,?zkaya, Bünyamin,Patureau, Frederic W.
-
supporting information
p. 3682 - 3687
(2021/02/01)
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- Elastase Inhibitor Cyclotheonellazole A: Total Synthesis and in Vivo Biological Evaluation for Acute Lung Injury
-
Acute lung injury/acute respiratory distress syndrome (ALI/ARDS) is one of the most common complications in COVID-19. Elastase has been recognized as an important target to prevent ALI/ARDS in the patient of COVID-19. Cyclotheonellazole A (CTL-A) is a nat
- Chen, Yue,Cui, Yingjun,Deng, Yangping,Fu, Qiang,Jiang, Peng,Li, Jing,Lin, Jianping,Liu, Yang,Meng, Qing,Sun, Yuanjun,Wang, Liang,Wang, Mukuo,Xu, Honglei,Ye, Baijun,Zhang, Mengyi,Zhang, Songming,Zhang, Tingrong,Zhao, Xiuhe
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-
- DEUTERIUM-ENRICHED SUBSTITUTED PHENOXYPHENYL ACETIC ACIDS AND ACYLSULFONAMIDES
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The present invention is concerned with deuterium-enriched substituted phenoxy-(3, 4-methylenedioxy)phenylacetic acid and acylsulfonamide derivatives of general structural formula I, their optically active or pure enantiomers and diastereomers, and pharmaceutical salts thereof, Formula (I) These compounds have selective antagonist activity for endothelin receptors or both endothelin and angiotensin II receptors, and are useful in the treatment of diseases mediated by endothelin and angiotensin-II and their receptors.
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Page/Page column 23; 32
(2021/06/22)
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- Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis
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The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.
- Daniliuc, Constantin G.,Gilmour, Ryan,Neufeld, Jessica,Sarie, Jér?me C.,Thiehoff, Christian
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supporting information
p. 15069 - 15075
(2020/06/17)
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- Nickel-catalyzed removal of alkene protecting group of phenols, alcohols via chain walking process
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An efficient nickel-catalyzed removal of alkene protection group under mild condition with high functional group tolerance through chain walking process has been established. Not only phenolic ethers, but also alcoholic ethers can be tolerated with the retention of stereocenter adjacent to hydroxyl group. The new reaction brings the homoallyl group into a start of new type of protecting group.
- Meng, Chenkai,Niu, Haolin,Ning, Juehan,Wu, Wengang,Yi, Jun
-
supporting information
(2020/02/04)
-
- Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates
-
The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.
- Hui, Zi,Jiang, Songwei,Qi, Xiang,Ye, Xiang-Yang,Xie, Tian
-
supporting information
(2020/05/18)
-
- 2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms
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The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 μg/ml; MIC(LORA) 2.06 and 1.59 μg/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 μM respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 μM respectively) followed by the Vit-K2 rescue study and ATP production assay.
- Datta, Dhrubajyoti,Debnath, Joy,Franzblau, Scott G.,Ghosh, Kalyan Sundar,Hari, Natarajan,Ma, Rui,Rana, Shiwani,Velappan, Anand Babu
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-
- A Structure-Reactivity Relationship of the Tandem Asymmetric Dihydroxylation on a Biologically Relevant Diene: Influence of Remote Stereocenters on Diastereofacial Selectivity
-
The Sharpless asymmetric dihydroxylation (AD) finds widespread use in natural product and drug molecule syntheses, in part, due to its efficiency and predictability. However, the tandem AD of dienes is much less studied, but important in complex molecular synthesis. Herein, a biologically relevant tandem AD is reported, and several anomalies are discovered with the accepted model. These include the formation of unpredicted diastereoisomers, with matched and mismatched stereocenters contradicting the Sharpless mnemonic device. From a structural analysis of the tandem AD, we present a strategy to improve asymmetric induction in sterically hindered alkenes using double diastereodifferentiation from a 9-bond distant stereocenter. A theoretical justification for the unpredicted stereoselectivity, accounting for the influence of steric hindrance and pre-installed chirality, is proposed.
- Gill, Daniel M.,Male, Louise,Jones, Alan M.
-
supporting information
p. 7568 - 7577
(2019/12/11)
-
- Design and phase transition behavior of siloxane-based monomeric and dimeric liquid crystals bearing cholesteryl mesogenic groups
-
A series of siloxane-based monomeric and dimeric liquid crystals (LCs) bearing cholesteryl mesogenic groups were newly synthesized and their phase transition behavior was investigated by polarized optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction (XRD). All the siloxane-based LCs obtained in this study showed a smectic A phase in a wide temperature range. Among the siloxane-based LCs obtained, only the dimeric LC with a shortest siloxane unit at a central part of a spacer was found to exhibit a chiral nematic phase and a blue phase in addition to the smectic A phase. The difference in the thermal properties of the siloxane-based dimeric LCs was investigated in terms of their conformations. Furthermore, the results obtained for the siloxane-based LCs were discussed with comparing with those of homologues having the normal alkyl chains and spacers.
- Katsuki, Kaito,Kaneko, Kosuke,Kaneko, Kimiyoshi,Kato, Riki,Miyamoto, Nobuyoshi,Hanasaki, Tomonori
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supporting information
p. 34 - 39
(2019/02/28)
-
- Semiheterogeneous Dual Nickel/Photocatalytic (Thio)etherification Using Carbon Nitrides
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A carbon nitride material can be combined with homogeneous nickel catalysts for light-mediated cross-couplings of aryl bromides with alcohols under mild conditions. The metal-free heterogeneous semiconductor is fully recyclable and couples a broad range of electron-poor aryl bromides with primary and secondary alcohols as well as water. The application for intramolecular reactions and the synthesis of active pharmaceutical ingredients was demonstrated. The catalytic protocol is applicable for the coupling of aryl iodides with thiols as well.
- Cavedon, Cristian,Madani, Amiera,Seeberger, Peter H.,Pieber, Bartholom?us
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supporting information
p. 5331 - 5334
(2019/07/08)
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- COMPOUNDS AND METHODS FOR REGULATING INSULIN SECRETION
-
Disclosed herein are methods for inducing insulin secretion in a glucose-dependent manner and compounds for use in these methods.
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Page/Page column 131; 132
(2018/10/19)
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- Nano-dispersed platinum(0) in organically modified silicate matrices as sustainable catalysts for a regioselective hydrosilylation of alkenes and alkynes
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Nano-dispersed platinum(0) particles stabilized in a range of organically modified silicate (ORMOSIL) matrices are investigated as sustainable catalysts for the hydrosilylation of alkenes and alkynes. In this study, five different siloxane matrices including triethoxysilane (HTEOS), methyltriethoxysilane (MTES), ethyltriethoxysilane (ETES), triethoxyvinylsilane (TEVS) and propyltriethoxysilane (PTES) are investigated, and the distribution of the metal particles in these materials analyzed by transition electron microscopy (TEM). The particles appeared to be generally of a small size, with a diameter of ca. 2-5 nm in each of these catalysts, however the distribution is not equally uniform from one matrix to the other. HTEOS, MTES and ETES that respectively carry a hydrogen, a methyl and an ethyl group on the triethoxysilane moiety, displayed a more uniform distribution, while particles appeared to be more scattered in the remaining matrices. Catalysts with a uniform particles distribution produced higher and consistent yields, while those with poor particles distribution produced lower and almost random yields, suggesting that the uniformity in particle distribution, and by extension the nature of the siloxane matrix, are important for the catalytic properties of these materials. The scope of the reaction was broadened to a range of olefins, with a goal of investigating the tolerability of the reaction toward a number of reactive functional groups, resulting in the preparation of 28 compounds. This catalytic system also enabled the hydrosilylation of a limited number of alkynes under the optimized reaction conditions.
- Duke, Brett J.,Akeroyd, Evan N.,Bhatt, Shreeja V.,Onyeagusi, Chibueze I.,Bhatt, Shreya V.,Adolph, Brandy R.,Fotie, Jean
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p. 11782 - 11795
(2018/07/25)
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- Identification of ortho-Substituted Benzoic Acid/Ester Derivatives via the Gas-Phase Neighboring Group Participation Effect in (+)-ESI High Resolution Mass Spectrometry
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Benzoic acid/ester/amide derivatives are common moieties in pharmaceutical compounds and present a challenge in positional isomer identification by traditional tandem mass spectrometric analysis. A method is presented for exploiting the gas-phase neighbor
- Blincoe, William D.,Rodriguez-Granillo, Agustina,Saurí, Josep,Pierson, Nicholas A.,Joyce, Leo A.,Mangion, Ian,Sheng, Huaming
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p. 694 - 703
(2018/04/14)
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- Designed Spiroketal Protein Modulation
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Spiroketals are structural motifs found in many biologically active natural products, which has stimulated considerable efforts toward their synthesis and interest in their use as drug lead compounds. Despite this, the use of spiroketals, and especially b
- Scheepstra, Marcel,Andrei, Sebastian A.,Unver, M. Yagiz,Hirsch, Anna K. H.,Leysen, Seppe,Ottmann, Christian,Brunsveld, Luc,Milroy, Lech-Gustav
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supporting information
p. 5480 - 5484
(2017/05/05)
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- A mild copper catalyzed method for the selective deprotection of aryl allyl ethers
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Copper boryl reagents enable the selective cleavage of aryl allyl ethers to the corresponding phenols in good to moderate yields.
- Hemming, David S.,Talbot, Eric P.,Steel, Patrick G.
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supporting information
p. 17 - 20
(2016/12/23)
-
- Design, synthesis and pharmacology of 1,1-bistrifluoromethylcarbinol derivatives as liver X receptor β-selective agonists
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A novel series of 1,3-bistrifluoromethylcarbinol derivatives that act as liver X receptor (LXR) β-selective agonists was discovered. Structure-activity relationship studies led to the identification of molecule 62, which was more effective (Emax) and selective toward LXRβ than T0901317 and GW3965. Furthermore, 62 decreased LDL-C without elevating the plasma TG level and significantly suppressed the lipid-accumulation area in the aortic arch in a Bio F1B hamster fed a diet high in fat and cholesterol. We demonstrated that our LXRβ agonist would be potentially useful as a hypolipidemic and anti-atherosclerotic agent. In this manuscript, we report the design, synthesis and pharmacology of 1,3-bistrifluoromethylcarbinol derivatives.
- Koura, Minoru,Matsuda, Takayuki,Okuda, Ayumu,Watanabe, Yuichiro,Yamaguchi, Yuki,Kurobuchi, Sayaka,Matsumoto, Yuuki,Shibuya, Kimiyuki
-
supporting information
p. 2668 - 2674
(2015/06/08)
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- An atom-economical and stereoselective domino synthesis of functionalised dienes
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Open sesame: A direct synthesis of functionalised and stereodefined dienes, relying on a domino allylic alkylation/electrocyclic ring-opening sequence, is reported. This method allows concise access to doubly vinylogous esters. A further systematic study
- Souris, Caroline,Luparia, Marco,Frebault, Frederic,Audisio, Davide,Fares, Christophe,Goddard, Richard,Maulide, Nuno
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supporting information
p. 6566 - 6570
(2013/07/05)
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- NiCl2·6H2O/NaBH4 in methanol: A mild and efficient strategy for chemoselective deallylation/debenzylation of aryl ethers
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Deprotection of allyl/benzyl aryl ethers was achieved chemoselectively. The mild and inexpensive reagent combination of NiCl2·6H 2O/NaBH4 in methanol afforded the products in high yields, within a reaction time of 5-10 min.
- Chouhan, Mangilal,Kumar, Kapil,Sharma, Ratnesh,Grover, Vikas,Nair, Vipin A.
-
supporting information
p. 4540 - 4543
(2013/08/23)
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- HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
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Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.
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Page/Page column 29
(2012/11/08)
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- SPIROCYCLIC GPR40 MODULATORS
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The present invention provides compounds useful, for example, for treating metabolic disorders in a subject. Such compounds have the general formula IA, IB, I'A or I'B, where the definitions of the variables are provided herein. The present invention also
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Page/Page column 295
(2010/04/30)
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- CARBINOL DERIVATIVES HAVING CYCLIC LINKER
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[Object] To provide a novel LXRβ agonist that is useful as a preventative and/or therapeutic agent for atherosclerosis; arteriosclerosis such as those resulting from diabetes; dyslipidemia; hypercholesterolemia; lipid-related diseases; inflammatory diseases that are caused by inflammatory cytokines; skin diseases such as allergic skin diseases; diabetes; or Alzheimer's disease. [Solving Means] A carbinol compound represented by the following general formula (I) or salt thereof, or their solvate.
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Page/Page column 13
(2010/03/31)
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- A new robust and versatile tetradentate linker for amides to be cleaved under mild conditions by unusual complexation of the amide nitrogen to Cu ++
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The concept of weakening amide bonds by the rather unusual forced complexation of nitrogen to Cu++ is not limited to tridentate ligands and was extended in this work to tetradentate ligands as well. The use of cyclic tetradentate ligands was to no avail, but an open-chain and more-flexible tetradentate ligand allowed mild cleavage by methanolysis after complexation. The principle was applied to the development of a new linker for solid-phase chemistry, which was proven to be extremely robust, yet allowed mild cleavage after activation by Cu ++ complexation. Its stability and versatility was demonstrated by the successful application to a whole plethora of different types of reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.
- Kramer, Rolf A.,Broehmer, Manuel C.,Forkel, Nina V.,Bannwarth
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experimental part
p. 4273 - 4283
(2011/02/25)
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- SUBSTITUTED CARBINOL COMPOUND
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There is provided a novel LXRβ agonist useful as a preventative and/or therapeutic agent for arteriosclerosis; arteriosclerosis such as those resulting from diabetes; hyperlipidemia; hypercholesterolemia; lipid-related diseases; inflammatory diseases caus
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Page/Page column 14
(2009/09/26)
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- Study on an electrorheological effect of side-chain polysiloxanes including fluorine atoms by the preshearing method
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Side-chain liquid-crystalline polysiloxane derivatives possessing fluorinated mesogens that have positive dielectric-anisotropy parallel to the long axis of mesogen were synthesized to study phase-transition behavior and electrorheological (ER) effect of the polymers with a preshearing method. About 2000Pa increments in shear stress could be obtained after preshearing as an ER effect. In addition, shear rate dependence on shear stress as a function of temperature was investigated. As a result, it was shown that the preshearing treatment with high shear rate was important to generate a larger ER effect.
- Kaneko, Kosuke,Miwa, Yusuke,Nakamura, Naotake
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- Facile and selective deallylation of allyl ethers using diphosphinidenecyclobutene-coordinated palladium catalysts
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(π-Allyl)palladium triflate bearing a 1,2-bis(4-methoxyphenyl)-3,4- bis(2,4,6-tri-tert-butylphenylphosphinidene)cyclobutene ligand (DPCB-OMe), [Pd(η3-C3H5)(DPCB-OMe)]OTf, efficiently catalyzes deallylation of a variety of allyl ethers in aniline to give corresponding alcohols in high yields under mild conditions. The reactions can be performed in air without loss of a variety of functionalities including vinyl, alkynyl, hydroxy, acetoxy, silyloxy, and acetal groups. Allyl 2-allyloxybenzoate selectively undergoes deallylation of the allyloxy group to give allyl salicylate in quantitative yield.
- Murakami, Hiromi,Minami, Tatsuya,Ozawa, Fumiyuki
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p. 4482 - 4486
(2007/10/03)
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- N-HYDROXYAMIDE DERIVATIVES POSSESSING ANTIBACTERIAL ACTIVITY
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Novel N-hydroxyamide derivatives are disclosed. These N-hydroxyamide derivatives inhibit UPD-3O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase, an enzyme present in gram negative bacteria and are therefore useful as antimicrobials and antibiotics. Methods of synthesis and of use of the compounds are also disclosed.
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- Peroxovanadium-catalyzed oxidative esterification of aldehydes
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The peroxovanadium species generated from V2O5 and hydrogen peroxide, which is liberated from peroxy salts such as sodium perborate (SPB) or sodium percarbonate (SPC), transform aldehydes directly into esters in an alcoholic medium. Monoesters of diols have been achieved directly in one pot from aldehydes. High catalytic turnover number combined with inexpensive, easily available reagents and innocuous side products from the reaction make it a suitable alternative for the synthesis of esters from aldehydes.
- Gopinath, Rangam,Barkakaty, Balaka,Talukdar, Bandana,Patel, Bhisma K.
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p. 2944 - 2947
(2007/10/03)
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- AMP deaminase inhibitors. 3. SAR of 3-(carboxyarylalkyl)coformycin aglycon analogues
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N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8- tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10- 100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy- 5-ethylphenyl)ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K(i) = 0.06 μM. The compounds within the series also exhibited > 1000-fold specificity for AMPDA relative to adenosine deaminase.
- Kasibhatla, Srinivas Rao,Bookser, Brett C.,Probst, Gary,Appleman, James R.,Erion, Mark D.
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p. 1508 - 1518
(2007/10/03)
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- THROMBIN INHIBITORS
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A compound which inhibits human thrombin and which has the general structure STR1
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- Endothelin antagonists bearing 5-membered heterocyclic amides
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Phenoxyphenylacetic acids and derivatives of the general structural formula I STR1 have endothelin antagonist activity and are useful in treating cardiovascular disorders, such as hypertension, postischemic renal failure, vasospasm, cerebral and cardiac i
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- ENDOTHELIN ANTAGONISTS BEARING PYRIDYL AMIDES
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Phenoxyphenylacetic acids and derivatives of the general structural formula I STR1 have endothelin antagonist activity and are useful in treating cardiovascular disorders, such as hypertension, postischemic renal failure, vasospasm, cerebral and cardiac i
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- Phenoxyphenylacetic acids and derivatives useful as endothelin antagonists.
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Phenoxyphenylacetic acids and derivatives of the general structural formula I STR1 have endothelin antagonist activity and are useful in treating cardiovascular disorders, such as hypertension, postischemic renal failure, vasospasm, cerebral and cardiac i
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- Quinazolinones substituted with phenoxyphenylacetic acid derivatives
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Phenoxyphenylacetic acids and derivatives of general structural formula I STR1 have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, postischemic renal failure, vasospasm, cerebal and card
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-
- QUINAZOLINONES SUBSTITUTED WITH PHENOXYPHENYLACETIC ACID DERIVATIVES
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Phenoxyphenylacetic acids and derivatives of general structural formula I STR1 have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, postischemic renal failure, vasospasm, cerebral and car
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- SIX MEMBERED RING FUSED IMIDAZOLES SUBSTITUTED WITH PHENOXYPHENYLACETIC ACID DERIVATIVES USED TO TREAT ASTHMA
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Phenoxyphenylacetic acids and derivatives of general structural formula I STR1 have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, congestive heart failure, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, inflammatory diseases, Raynaud's disease, and endotoxic shock, and asthma.
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- Silanol compounds, polymerizable monomers and polymers having mesogenic groups
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A silanol compound having a mesogenic group, of the following formula (III): STR1 wherein each of R5 and R6, which may be the same or different, is an alkyl group or a phenyl group, X is a single bond, an oxygen atom, or a group of t
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- TRIAZOLE ANGIOTENSIN II ANTAGONISTS INCORPORATING A SUBSTITUTED BENZYL ELEMENT
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Substituted triazoles attached through a methylene bridge to novel substituted phenyl derivatives of the Formula I, are useful as angiotensin II antagonists. STR1
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- ANGIOTENSIN II ANTAGONISTS INCORPORATING A SUBSTITUTED PYRIDOIMIDAZOLYL RING
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Substituted heterocycles attached through a methylene bridge to novel substituted phenyl derivatives of the Formula I are useful as angiotensin II antagonists. STR1
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- QUINAZOLINONE, TRIAZOLINONE AND PYRIMIDINONE ANGIOTENSIN II ANTAGONISTS INCORPORATING A SUBSTITUTED BENZYL ELEMENT
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Substituted heterocycles attached through a methylene bridge to novel substituted phenyl derivatives of the Formula I are useful as angiotensin II antagonists. STR1
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- 6-(1-ACYL-1-HYDROXYMETHYL)PENICILLANIC ACID DERIVATIVES
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6-(1-Acyl-1-hydroxymethyl)penicillanic acid derivatives are useful as antibacterials and/or beta-lactamase inhibitors.
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