101166-65-8Relevant academic research and scientific papers
A concise synthesis of the pentacyclic framework of cortistatins
Yamashita, Shuji,Iso, Kentaro,Hirama, Masahiro
, p. 3413 - 3415 (2008)
(Chemical Equation Presented) An efficient synthesis of the pentacyclic framework of cortistatins has been developed. The key strategy comprises assembly of the A- and the CD-ring fragments by Knoevenagel reaction, facile formation of the pyran ring via e
A strategy towards the synthesis of plumarellide based on biosynthesis speculation, featuring a transannular 4+2 type cyclisation from a cembranoid furanoxonium ion intermediate
Li, Yi,Palframan, Matthew J.,Pattenden, Gerald,Winne, Johan M.
, p. 7229 - 7240 (2014)
In studies towards a biomimetic synthesis of plumarellide 1, acid-catalysed rearrangement of the furanobutenolide-based acetonide 10b led to the ring system 15b in plumarellide together with the cycloheptene-based ring system 11 found in rameswaralide 4, in a combined yield of 60%. RCM of the ω-dienes 30a and 30b led to the macrocycles 38a and 38b, respectively with the Z-configuration. Treatment of the vinyl bromide/vinyl stannanes 32a and 47 under Stille conditions failed to give the macrocycles 31a and 48, respectively. Reactions of the macrocycles 38a and 38b with TFA containing water produced the 5,6,7-tricyclic compounds 56a and 56b, respectively in >90% yield, instead of the plumarellide-based ring system 52. A summary and perspective on possible pathways from the C-13 acetoxy furanocembranoid 66 and from the C13–C14 unsaturated enol ether/cyclic hemiketal 9/59 to plumarellide 1 in vivo is given.
Cyclic ethers as educts for the synthesis of lepidoptra pheromones
Poleschner,Heydenreich,Martin
, p. 1231 - 1235 (1991)
ω-Iodo(trialkylsiloxy)alkanes 2 prepared by ring opening of cyclic ethers with iodotrimethylsilane, are useful starting materials for the synthesis of pheromone components. Reaction with triphenylphosphine to give the corresponding Wittig reagent and subsequent coupling with lithium (Z)-dihex-1-enylcuprate gives (Z)-alken-1-ols 5 and 7, after deprotection, in good yields. The direct coupling of 2 with alkynes failed because of competition reactions, however, the more stable ω-iodo-1-(tert-butyldimethylsiloxy)alkanes were able to undergo C,C-coupling with alkynes. The thus formed 1-(tert-butyldimethylsiloxy)-5-decyne (13c) was hydrogenated and deprotected to give (E)-5-decen-1-ol (15c).
A Copolymerized Dodecacarborane Anion as Covalently Attached Cation Exchanger in Ion-Selective Sensors
Qin, Yu,Bakker, Eric
, p. 6002 - 6010 (2003)
The traditional cation exchangers used in ion-selective electrodes and optodes are tetraphenylborate derivatives, which are generally adequate for most analytical applications but may in some cases suffer from decomposition by acid hydrolysis, oxidants, and light. Recently, halogenated dodecacarboranes were found to be improved cation exchangers in terms of lipophilicity and chemical stability. This forms the basis for the convenient covalent attachment of the cation exchanger to the polymeric backbone of the sensing material. This is a challenge that has not satisfactorily been solved and which is especially important in view of developing ultraminiaturized sensing arrays. Here, a C-derivative of the closo-dodecacarborane anion (CB11H 12-) with a polymerizable group was synthesized as a chemically stable cation exchanger. This new derivative was copolymerized with methyl methacrylate and decyl methacrylate (MMA-DMA) to fabricate a plasticizer-free polymer with cation-exchange properties. This polymer could be conveniently blended with traditional plasticized poly(vinyl chloride) or with noncrosslinked methacrylic polymers to give solvent cast films that appear to be clear and homogeneous and that could be doped with ionophores. Optode leaching experiments supported the covalent grafting of the carborane anions. Ion-selective membranes and optode thin films were evaluated in terms of response function, response time, and selectivity. In all cases, the new material exhibited behavior similar to free tetraphenylborate derivative-based membranes. As a result of these studies, an all-polymeric plasticizer-free calcium-selective membrane was fabricated on the basis of the covalently attached carborane, a recently introduced grafted calcium ionophore, and an MMA-DMA polymer matrix. The resulting ion-selective electrodes showed Nernstian response slopes and rapid response times, demonstrating that covalent grafting of all sensing components is a feasible approach to the development of ion sensors.
COMPOUNDS AS INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR
-
Paragraph 081, (2020/09/27)
The present invention provides compounds of Formula (I) shown above and their pharmaceutically acceptable salt, solvates, isomers, or prodrugs, as well as pharmaceutical compositions containing these compounds. Also provided by the invention is a method for treating a disorder mediated by macrophage migration inhibitory factor in a subject, comprising administering to the subject in need thereof a compound or a pharmaceutical composition of this invention.
Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones
Huynh, Uyen,McDonald, Stacey L.,Lim, Daniel,Uddin, Md. Nasir,Wengryniuk, Sarah E.,Dey, Sumit,Coltart, Don M.
, p. 12951 - 12964 (2018/11/30)
The α-alkylation of ketones is a fundamental synthetic transformation. The development of asymmetric variants of this reaction is important given that numerous natural products, drugs, and related compounds exist as α-functionalized ketones or derivatives thereof. We previously reported our preliminary studies on the development of a new enantioselective ketone α-alkylation procedure using N-amino cyclic carbamate (ACC) auxiliaries. In comparison to other auxiliary-based methods, ACC alkylation offers a number of advantages and is both highly enantioselective and high yielding. Herein, we provide a full account of our studies on the enantioselective ACC ketone α-alkylation method.
Evolution of a Polyene Cyclization Cascade for the Total Synthesis of (?)-Cyclosmenospongine
Speck, Klaus,Magauer, Thomas
supporting information, p. 1157 - 1165 (2017/02/05)
We report a full account on the development of a unique cationic polyene cyclization for the total synthesis of the tetracyclic meroterpenoid (?)-cyclosmenospongine. A highly convergent three-component coupling strategy enabled rapid access to individual cyclization precursors that were tested for their reactivity. The successful transformation generates three rings and sets four consecutive stereocenters in a single operation proceeding in a highly efficient manner to give exclusively the trans-decalin framework. In addition, we found that the enol ether geometry and the relative configuration of C3 and C8 are crucial for the success of the polyene cyclization.
Synthesis of Macrocyclic Lactones via Ring Transformation of 4-(ω-Hydroxyalkyl)-1,3-oxazol-5(4H)-ones
Fritschi, Stephan P.,Linden, Anthony,Heimgartner, Heinz
, p. 523 - 538 (2016/07/22)
The synthesis of α-benzamido-α-benzyl lactones 23 of various ring size was achieved either via ‘direct amide cyclization’ by treatment of 2-benzamido-2-benzyl-ω-hydroxy-N,N-dimethylalkanamides 21 in toluene at 90 – 110° with HCl gas or by ‘ring transformation’ of 4-benzyl-4-(ω-hydroxyalkyl)-2-phenyl-1,3-oxazol-5(4H)-ones under the same conditions. The precursors were obtained by C-alkylations of 4-benzyl-2-phenyl-1,3-oxazol-5(4H)-one (15) with THP- or TBDMS-protected ω-hydroxyalkyl iodides. Ring opening of the THP-protected oxazolones by treatment with Me2NH followed by deprotection of the OH group gave the diamides 21, whereas deprotection of the TBDMS series of oxazolones 25 with TBAF followed by treatment with HCl gas led to the corresponding lactones 23 in a one-pot reaction.
PYRIDINE DERIVATIVES AS DGAT-1 INHIBITORS
-
Page/Page column 20; 38, (2014/09/29)
Described herein are compounds of formula (I): The compounds of formula (I) act as DGAT1 inhibitors and can be useful in preventing, treating or acting as a remedial agent for hyperlipidemia, diabetes mellitus and obesity.
NOVEL ANTIVIRAL PYRROLOPYRIDINE DERIVATIVES AND METHOD FOR PREPARING THE SAME
-
Paragraph 0234, (2014/09/16)
The present invention relates to a pyrrolopyridine derivative represented by the Chemical Formula I, and a racemate or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, and relates to an antiviral composition including the same as an active ingredient. The compound of the Chemical Formula I has excellent antiviral activity and selectivity for wild type and resistant HIV-1, and thereby is useful as a therapeutic agent for acquired immune deficiency syndrome (AIDS).
