- Highly diastereoselective mercury-mediated synthesis of functionalized 2-azabicyclo[3.3.0]octane derivatives
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In this paper we described the synthesis of the cis-2-azabicyclo[3.3.0]octane derivative (5b) employing highly diastereoselective mercury(II)-mediated intramolecular amino-cyclization, followed by reductive demercuration of ethyl erythro-1-allyl-2-amino-1
- Pe?anha, Emerson P,Verli, Hugo,Rodrigues, Carlos R,Barreiro, Eliezer J,Fraga, Carlos A.M
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Read Online
- Studies toward the diastereoselective reduction of 2-alkoxycarbonyl-2-allyl-cyclopentanone derivatives with boron hydrides
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The reduction of 2-alkoxycarbonyl-2-allyl-cyclopentanone derivatives with inexpensive boron hydrides were studied showing that this process depend on chelation factors instead steric ones, affording the isomeric alcohols 2a and 3a with high diastereomeric
- Fraga,Barreiro
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Read Online
- Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer's disease: Design, synthesis and biological evaluation
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A series of new coumarin-dithiocarbamate hybrids were designed and synthesized as multitarget agents for the treatment of Alzheimer's disease. Most of them showed potent and clearly selective inhibition towards AChE and MAO-B. Among these compounds, compound 8f demonstrated the most potent inhibition to AChE with IC50 values of 0.0068 μM and 0.0089 μM for eeAChE and hAChE, respectively. Compound 8g was identified as the most potent inhibitor to hMAO-B, and it is also a good and balanced inhibitor to both hAChE and hMAO-B (0.114 μM for hAChE; 0.101 μM for hMAO-B). Kinetic and molecular modeling studies revealed that 8g was a dual binding site inhibitor for AChE and a competitive inhibitor for MAO-B. Further studies indicated that 8g could penetrate the BBB and exhibit no toxicity on SH-SY5Y neuroblastoma cells. More importantly, 8g did not display any acute toxicity in mice at doses up to 2500 mg/kg and could reverse the cognitive dysfunction of scopolamine-induced AD mice. Overall, these results highlighted 8g as a potential multitarget agent for AD treatment and offered a starting point for design of new multitarget AChE/MAO-B inhibitors based on dithiocarbamate scaffold.
- He, Qi,Liu, Jing,Lan, Jin-Shuai,Ding, Jiaoli,Sun, Yongbing,Fang, Yuanying,Jiang, Neng,Yang, Zunhua,Sun, Liyuan,Jin, Yi,Xie, Sai-Sai
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supporting information
p. 512 - 528
(2018/09/29)
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- On the ozonolysis of unsaturated tosylhydrazones as a direct approach to diazocarbonyl compounds
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The scope and limitations are described of reacting unsaturated tosylhydrazones with O3 followed by Et3N for the generation of 1,4- and 1,5-diazocarbonyl systems. Tosylhydrazones, from tosylhydrazide condensation with readily available δ- and ?-unsaturated α-ketoesters, led in the former case to a 2-pyrazoline whereas the latter cases led to α-diazo-?-ketoesters, although a terminal alkene produced a tetrahydropyridazinol. Using the ozonolysis-Et3N strategy, tosylhydrazones from cyclic enones give 2,5- and 2,6-diazoketones with aldehyde or ester functionality at the 1-position; the α-diazoaldehydes prefer the s-trans conformation, with a rotation barrier of 74 kJ mol-1 at 25 °C determined by NMR. This one-pot ozonolysis/Bamford-Stevens chemistry demonstrates both the tolerance of tosylhydrazones to ozone, and the subsequently added amine playing a dual role to directly transform the intermediate tosylhydrazone ozonides into products containing reactive diazo and ketone functionalities; such adducts are of particular value as precursors to cyclic carbonyl ylides for 1,3-dipolar cycloadditions.
- Fegheh-Hassanpour, Younes,Ebrahim, Faisal,Arif, Tanzeel,Sintim, Herman O.,Claridge, Timothy D. W.,Amin, Nader T.,Hodgson, David M.
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p. 2876 - 2884
(2018/05/03)
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- Phosphate tricyclic coumarin analogs as steroid sulfatase inhibitors: Synthesis and biological activity
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In the present work, we report convenient methods for the synthesis and biological evaluation of phosphate tricyclic coumarin derivatives as potential steroid sulfatase inhibitors. The described synthesis includes the straightforward preparation of 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one, 3-hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-8,9,10,11-tetrahydro-7H-cyclohepta[c]chromen-6-one modified with various phosphate moieties. The inhibitory effects of the synthesized compounds were tested on STS isolated from human placenta as well as the MCF-7, MDA-MB-231 and MDA-MB-435S cancer cell lines. Most of the new STS inhibitors possessed IC50 values between 21 to 159 μM. In the course of our investigation, the largest inhibitory effects in the STS enzyme assays were observed for the three compounds 9p, 9r and 9s, with IC50 values of 36.4, 37.8 and 21.5 μM, respectively (IC50 value of 1.0 μM for the 665-COUMATE used as a reference). The compound 9r, exhibited the highest potency against MCF-7, an estrogen receptor positive (ER+) cell line, with a GI50 value of 24.7 μM. The structure-activity relationships of the synthesized coumarin derivatives with the STS enzyme are discussed.
- Kozak, Witold,Dasko, Mateusz,Maslyk, Maciej,Pieczykolan, Jerzy S.,Gielniewski, Bartlomiej,Rachon, Janusz,Demkowicz, Sebastian
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p. 44350 - 44358
(2014/12/10)
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- 1-(Arylmethyl)-5,6,7,8-tetrahydroquinazolline-2,4-diones and Analogs and the Use Thereof
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Disclosed are novel 1-(arylmethyl)-5,6,7,8-tetrahydroquinazoline-2,4-diones and analogs thereof, represented by the Formula I, wherein Ar, A, B, R3-R6 are defined herein. Compounds having Formula I are PARP inhibitors. Therefore, compounds of the invention may be used to treat clinical conditions that are responsive to the inhibition of PARP activity, such as cancer.
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Paragraph 0151; 0199
(2014/09/30)
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- Synthesis of five-and six-membered 1,3,3-trimethyl-2-(trimethylsilyl) cycloalkenes: A novel preparation of alkyl/alkenyl/aryl 2,5,5-trimethyl-1- cyclopentenyl ketones
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1,3,3-trimethyl-2-(trimethylsilyl)cyclopentene and 1,3,3-trimethyl-2- -(trimethylsilyl)cyclohexene were prepared in good yields by the Wurtz-Fittig coupling reaction of the corresponding 2-iodo-1,3,3-trimethylcyclopentene and 2-chloro-1,3,3-trimethylcyclohexene with metallic sodium and chlorotrimethylsilane in anhydrous ether solvent. The Friedel-Crafts acylation reaction of 1,3,3-trimethyl-2-(trimethylsilyl)cyclopentene with six different acid chlorides and the novel preparation of six alkyl/alkenyl/aryl 2,5,5-trimethyl-1-cyclopentenyl ketones are reported.
- Venkatesha, Manjunatha A.,Suresh, Hariprasad
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p. 759-768+S57-S61
(2013/07/26)
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- 1-(ARYLMETHYL)-5,6,7,8-TETRAHYDROQUINAZOLINE-2,4-DIONES AND ANALOGS AND THE USE THEREOF
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Disclosed are novel 1-(arylmethyl)-5,6,7,8-tetrahydroquinazoline-2,4-diones and analogs thereof, represented by the Formula I, wherein Ar, A, B, R3-R6 are defined herein. Compounds having Formula I are PARP inhibitors. Therefore, compounds of the invention may be used to treat clinical conditions that are responsive to the inhibition of PARP activity, such as cancer.
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Page/Page column 23; 33
(2013/05/22)
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- 2-METHYLENE-5-SUBSTITUTED-METHYLENECYCLOPENTANONE DERIVATIVES AND USE THEREOF
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The invention relates to 2-methylene-5-substituted-methylenecyclopentanone derivatives of formula I, and the use thereof. The derivatives of formula I as active components are useful for preparing a medicine for the treatment and/or prevention of cancer diseases such as breast cancer, lung cancer, colon cancer, rectal cancer, stomach cancer, prostate cancer, bladder cancer, uterus cancer, pancreatic cancer and ovary cancer. The active compounds of the invention may be used as an anticancer drug alone or used in combination with one or more other antitumor drugs. A combined therapy can be carried out by administrating each therapeutic component concurrently, subsequently or separately.
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(2011/04/18)
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- 2-METHYLENE-5-SUBSTITUTED METHYLENE CYCLOPENTANONE DERIVATIVES AND USE THEREOF
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The invention relates to 2-methylene-5-substituted-methylenecyclopentanone derivatives of formula I, and the use thereof. The derivatives of formula I as active components are useful for preparing a medicine for the treatment and/or prevention of cancer diseases such as breast cancer, lung cancer, colon cancer, rectal cancer, stomach cancer, prostate cancer, bladder cancer, uterus cancer, pancreatic cancer and ovary cancer. The active compounds of the invention may be used as an anticancer drug alone or used in combination with one or more other antitumor drugs. A combined therapy can be carried out by administrating each therapeutic component concurrently, subsequently or separately.
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Page/Page column 16-17
(2010/11/19)
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- Ionic liquid promoted selective debromination of α-bromoketones under microwave irradiation
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The debromination of α-bromoketones with an easily accessible ionic liquid, 1-methyl-3-pentylimidazolium tetrafluoroborate, [pmIm]BF4 under microwave irradiation has been investigated. By controlling the reaction time gem-α-dibromoketones are selectively debrominated to either monobromo or debromoketones. The α-monobromo- and α-monoiodoketones are dehalogenated while the corresponding chloroketones remain inert. The activated vic-bromoacetates are converted to the corresponding (E)-alkenes by the same procedure. These reactions do not require any organic solvent, any metal or any conventional reducing agent. The ionic liquid works here as catalyst as well as reaction medium and is recycled without any appreciable loss of its catalytic efficiency.
- Ranu, Brindaban C.,Chattopadhyay, Kalicharan,Jana, Ranjan
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p. 155 - 159
(2007/10/03)
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- Process for preparing cyclic ketones
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The present invention provides a process for preparing cyclic 1,3-keto esters in the absence of solvent, using solid-state or high viscosity reactors.
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Page/Page column 4
(2008/06/13)
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- Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles
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A stereospecific palladium-catalyzed N-vinylation of aza-heterocycles with vinyl inflates is described. Cyclic and acyclic vinyl triflates along with nonnucleophilic azaheterocycles were found to be substrates for this palladium-catalyzed synthesis of N-vinyl pyrrole and indole derivatives.
- Movassaghi, Mohammad,Ondrus, Alison E.
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p. 8638 - 8641
(2007/10/03)
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- A simple, efficient and general procedure for acetalization of carbonyl compounds and deprotection of acetals under the catalysis of indium(III) chloride
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Indium (III) chloride efficiently catalyzes the protection of a variety of aldehydes and ketones to their corresponding 1,3-dioxolanes and dialkyl acetals in refluxing cyclohexane. On the other hand, deprotection of acetals is also achieved in refluxing aqueous methanol under the catalysis of indium(III) chloride.
- Ranu, Brindaban C.,Jana, Ranjan,Samanta, Sampak
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p. 446 - 450
(2007/10/03)
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- Palladium-Catalyzed Amidation of Enol Triflates: A New Synthesis of Enamides
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(Matrix presented) The palladium-catalyzed coupling of a range of enol triflates with amides, carbamates, and sulfonamides has been developed. This offers a simple and widely applicable synthesis of enamides, which may not be readily available by other me
- Wallace, Debra J.,Klauber, David J.,Chen, Cheng-Yi,Volante, Ralph P.
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p. 4749 - 4752
(2007/10/03)
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- Method for preparing chiral diphosphines
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The invention concerns a method for preparing a compound of formula (1) wherein: A represents naphthyl or phenyl optionally substituted; and Ar1, Ar2independently represent a saturated or aromatic carbocyclic group, optionally substituted.
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- Preparation of cycloalkanone oxime ethers via a free radical acylation approach
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Abstract: Radical-mediated annulation approaches for the formation of cycloalkanone oxime ethers are described. Based on radical acylation approaches, α-functionalized cycloalkanone oxime ethers, 1,3- and 1,4-cyclohexanedione oxime ethers are prepared.
- Kim,Kim,Yoon,Oh
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p. 1148 - 1150
(2007/10/03)
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- Tetrabutylammonium peroxydisulfate in organic synthesis; VII. A facile and efficient method for the regeneration of carbonyl compounds from semicarbazones by tetrabutylammonium peroxydisulfate
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Semicarbazones of aldehydes and ketones are oxidized to the corresponding carbonyl compounds in excellent yields by tetrabutylammonium peroxydisulfate in dichlorlethane under mild conditions.
- Chen, Fen-Er,Liu, Ji-Dong,Fu, Han,Peng, Zuo-Zhong,Shao, Lan-Ying
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p. 2295 - 2299
(2007/10/03)
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- Asymmetric hydrogenation method of a ketonic compound and derivative
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The present invention relates to a process for the asymmetric hydrogenation of a ketonic compound and derivative. The invention relates to the use of optically active metal complexes as catalysts for the asymmetric hydrogenation of a ketonic compound and derivative. The process for the asymmetric hydrogenation of a ketonic compound and derivative is characterized in that the asymmetric hydrogenation of said compound is carried out in the presence of an effective amount of a metal complex comprising as ligand an optically active diphosphine corresponding to one of the following formulae: STR1
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- Tetrabutylammonium peroxydisulfate in organic synthesis; IV. An efficient, highly selective and oxidative deoximation by tetrabutylammonium peroxydisulfate
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Tetrabutylammonium peroxydisulfate has been proved out to be an efficient and highly chemoselective reagent for the conversion of oximes to the corresponding carbonyl compounds under mild conditions.
- Chen, Fener,Liu, Anchang,Yan, Qiongjiao,Liu, Mingxing,Zhang, Daoming,Shao, Lanying
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p. 1049 - 1056
(2007/10/03)
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- Solvent-free Dieckmann condensation reactions of diethyl adipate and pimelate
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Dieckmann condensation reactions of diethyl adipate and pimelate proceeded efficiently in the absence of solvent, and the reaction products were collected by a direct distillation from the solvent-free reaction mixture.
- Toda, Fumio,Suzuki, Takaaki,Higa, Satoru
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p. 3521 - 3522
(2007/10/03)
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- Convenient preparation of metals deposited on solid supports and their use in organic synthesis
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'High-surface alkali metals' can be conveniently prepared via deposition of corresponding metals on various supports such as sodium chloride, polyethylene, polypropylene and cross-linked polystyrene from their solutions in liquid ammonia. Alkali metals deposited on polymeric supports can be stored in form of stable suspensions in inert solvents and used for the acyloin and Dieckmann condensations and for preparation of organolithiums. Addition of the suspension of supported alkali metal to a solution of zinc chloride gave an active zinc on polymeric support, which can be used for the Reformatski and Barbier reactions.
- Majkosza, Mieczyslaw,Nieczypor, Piotr,Grela, Karol
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p. 10827 - 10836
(2007/10/03)
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- The reaction of α-diazo-β-hydroxy esters with boron trifluoride etherate: Generation and rearrangement of destabilized vinyl cations. A detailed experimental and theoretical study
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Cyclic ethyl 2-diazo-3-hydroxy carboxylates were prepared by treating ethyl diazoacetate with LDA followed by reaction with a series of cyclic ketones. Further treatment of these α-diazo-β-hydroxy esters with boron trifluoride etherate in various solvents affords an unusual array of products. Product types and ratios were found to be strongly dependent on ring size and the solvent used. The reaction proceeds by Lewis acid complexation of the alcohol functionality of the diazo hydroxy ester with BF3 etherate followed by neighboring-group participation of the diazo moiety to generate a cycloalkylidene diazonium salt. Loss of nitrogen produces a highly reactive, destabilized, linear vinyl cation. Ring expansion via a 1,2-methylene shift leads to the formation of a more stable, bent cycloalkenyl vinyl cation. A subsequent 1,2-methylene shift results in ring contraction ultimately leading to a stable allylic cation. This cation is either trapped by the solvent or else undergoes cyclization with the adjacent ester group to give a lactone. Computational studies at the 6-31G* level were performed to determine the geometry of the optimized vinyl cations. Relative energies suggest a moderate energy gain for isomerization of the initial vinyl cation V1 to the rearranged vinyl cation V2 followed by a large stabilization in energy for subsequent conversion to the allyl cation A1. Compared with isolated product distributions, the energy profiles suggest kinetically-controlled V1 → V2 → A1 migrations. Finally, the calculations suggest that in diethyl ether the carbocations may be coordinated to a molecule of solvent resulting in "protected" cationic intermediates with nonlinear geometries.
- Pellicciari, Roberto,Natalini, Benedetto,Sadeghpour, Bahman M.,Marinozzi, Maura,Snyder, James P.,Williamson, Bobby L.,Kuethe, Jeffrey T.,Padwa, Albert
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- Simple and rapid determination of the activation parameters of organic reactions by temperature-dependent NMR spectroscopy II. Application to reversible reactions
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A non-isothermal (NIT) method for evaluating the activation enthalpies and entropies of reactions in solutions was applied to several reversible reactions. This was realized by a stepwise elevation of the temperature of a reaction system using a variable-temperature apparatus comprising on NMR spectrometer and a quick collection of FID (free induction decay) at every plateau of the step. The rate from NIT experiments agreed well with the previously measured rates by the conventional methods.
- Satoh, Masahiro,Hirota, Minoru
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p. 2619 - 2624
(2007/10/03)
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- Benzopyranones, a method for producing them and uses therefor
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Novel 2H-1-benzopyran-2-ones (coumarin derivatives) of the general formula (I) are provided: STR1 wherein R1, R2, R3, R4, X and Y are defined as in the specification, and the addition compounds thereof with physiologically compatible acids, intermediates and methods for the preparation thereof. The coumarin compounds possess a neuroprotective and anti-allergic action.
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- Chemoselective Dieckmann-like condensations using N-methoxy-N-methylamides
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The use of N-methoxy-N-methylamide as a chemoselective group in Dieckmann-like condensation is described. The chemoselectivity in these cyclizations is dependent on the counterion of the base employed.
- Sibi, Mukund P.,Christensen, James W.,Kim, Sung-Gyu,Eggen, Marijean,Stessman, Chad,Oien, Larry
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p. 6209 - 6212
(2007/10/02)
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- Synthesis of aldehydes from carboxylic acids via N-methoxyimidoyl bromides: Deoximation of O-methyloximes
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Aldehydes are synthesized by hydrogenation and subsequent deoximation of substituted N-methoxyalkanimidoyl bromides, which are prepared in one pot by reaction of the corresponding carboxylic acids with methoxyamine and triphenylphosphine carbon tetrabromide. Regeneration of aldehydes and ketones from O-methyloximes under mild conditions is also described.
- Sakamoto,Kikugawa
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p. 563 - 564
(2007/10/02)
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- Mechanism of action of vitamin K
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Vitamin K is the blood clotting vitamin; it to important as an obligatory cofactor for the which Carboxylates selected glutamate residues In the proteins of the blood coagulation cascade, including prothrombin (factor II), factors VII, IX, and X and prote
- Dowd, Poul,Ham, Seung Wook,Geib, Steven J.
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p. 7734 - 7743
(2007/10/02)
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- Mechanism of hydrolysis and structure-stability relationship of enaminones as potential prodrugs of model primary amines
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The objective of this work was to investigate the chemistry and the structure-stability relationship of enaminones (a class of enamines formed between a primary amine and a 1,3-dicarbonyl compound) and to evaluate their potential usefulness as prodrugs of primary amines. The acid-catalyzed degradation of the enaminones was found to be very sensitive to minor differences in the structure of the 1,3-dicarbonyl compound used to form the enaminone, but relatively insensitive to changes in the amine portion of the enaminones. A correlation was found between the rate of enaminone hydrolysis and the pK(a) of the 1,3-dicarbonyl compound, suggesting that the rate-controlling step in the hydrolysis of the enaminones was the proton addition to the vinyl carbon of the enaminone. Enaminones formed with cyclic 1,3-dicarbonyl compounds were significantly more stable than those formed with structurally similar acyclic compounds. Based on chemical stability considerations alone, enaminones do not appear to be good candidates as prodrugs of primary amines. Evidence is presented, however, that enaminones formed between amines and 1,3-ketoesters or lactones may be subject to enzyme-catalyzed degradation. Further research on the design of enaminones destabilized by a triggering enzymatic event that results in the loss of conjugation (e.g., ester or lactone hydrolysis or an oxidation/reduction event) may prove worth pursuing.
- Naringrekar,Stella
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p. 138 - 146
(2007/10/02)
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- ULTRASOUND IN ORGANIC SYNTHESIS 5. PREPARATION AND SOME REACTIONS OF COLLOIDAL POTASSIUM
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colloidal potassium is easily obtained by ultrasonic irradiation in toluene.Some of its reactions with organic substrates are given.
- Luche, J.L.,Petrier, C.,Dupuy, C.
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p. 753 - 756
(2007/10/02)
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- A DIRECTION CONTROLLED DIECKMANN TYPE CYCLIZATION OF HALF-THIOL DIESTERS
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A direction controlled Dieckmann type cyclization was performed on treatment of the half-thiol diesters(1) with base to give exclusively the β-keto esters(2).
- Yamada, Yasuji,Ishii, Toshihide,Kimura, Masayuki,Hosaka, Kunio
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p. 1353 - 1354
(2007/10/02)
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- Hydro substituted prostanoic acids and esters
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This disclosure describes certain 11-hydroxy and 11-deoxy-9-keto (or hydroxy)prostanoic acid derivatives useful as bronchodilators, anti-ulcer agents, or as intermediates.
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- Novel 11-hydroxy-9-keto-5,6-cis-13,14-cis-prostadienoic acid derivatives
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This disclosure describes certain 11-hydroxy and 11-deoxy-9-keto(or hydroxy)-prostanoic acid derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents, or as intermediates.
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- Derivatives of 9-hydroxy-13-trans-prostenoic acid
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This disclosure describes certain 15-deoxy prostanoic acid derivatives having a hydroxy group further along in the beta-chain, useful as bronchodilators, hypotensive agents, anti-ulcer agents, or as intermediates.
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- 3-Alkyl-2-(6-carboxyhexyl)cyclopentanones and esters and salts thereof
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This disclosure describes compounds of the class of substituted 9-oxoprostanoic acids and the esters and cationic salts thereof, useful as antimicrobial agents, hypotensive agents, anti-ulcer agents, or as intermediates, and novel processes for preparing the same.
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- 1-Alkoximino-2-(ω-substituted alkyl)-2-cyclopentenes
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This disclosure describes certain 1-alkoximino-2-(ω-substituted-alkyl)-2-cyclopentenes useful as intermediates for the preparation of homologues, analogues, congeners, and derivatives of 9-oxo-13-trans-prostenoic acid and of 9-hydroxy-13-trans-prostenoic acid which have antimicrobial activity and prostaglandin-like hypotensive activity.
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- 11-Deoxy-13-dihydro-prostaglandin-9-ketals
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This disclosure describes novel 11-deoxy-13,14-dihydro-prostaglandin-9-ketals useful as bronchodilators and as gastric acid secretion inhibitors.
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- Novel 15-substituted prostanoic acids and esters
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This disclosure describes compounds of the class of 15-substituted-9-keto(or 9-hydroxy)prostanoic acids and the esters and cationic salts thereof, useful as inhibitors of gastric acid secretion.
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- Lithium 3-triphenylmethoxy-1-trans-alkenyl-dialkyl alanates
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This disclosure describes 3-triphenylmethoxy-1-alkynes, 3-triphenylmethoxy-1-trans-alkenyl-dialkyl-alanes, and lithium 3-triphenylmethoxy-1-trans-alkenyl-dialkyl alanates useful as intermediates for the preparation of certain 11-hydroxy- and 11-deoxy-9-keto(or hydroxy)-prostanoic acid derivatives which possess bronchodilator, hypotensive, and anti-ulcer activity.
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- Hydroxylated 15-deoxy derivatives of 9-hydroxy-13-trans-prostenoic acid
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This disclosure describes certain 15-deoxy prostanoic acid derivatives having a hydroxy group further along in the beta-chain, useful as bronchodilators, hypotensive agents, anti-ulcer agents, or as intermediates.
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