128217-23-2Relevant articles and documents
IMIDAZOLE COMPOUND
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Paragraph 0112-0113; 0194-0195, (2018/03/25)
Disclosed is an imidazole compound, in particular, the compound as shown in formula (I) and a pharmaceutically acceptable salt or tautomer thereof are disclosed.
Rhodium-catalyzed endo -selective epoxide-opening cascades: formal synthesis of (-)-brevisin
Armbrust, Kurt W.,Beaver, Matthew G.,Jamison, Timothy F.
supporting information, p. 6941 - 6946 (2015/06/16)
[Rh(CO)2Cl]2 is as an effective catalyst for endo-selective cyclizations and cascades of epoxy-(E)-enoate alcohols, thus enabling the synthesis of oxepanes and oxepane-containing polyethers from di- and trisubstituted epoxides. Synth
Stereoselective synthesis of conjugated trienols from allylic alcohols and 1-iodo-1,3-dienes
Brandt, Damien,Bellosta, Veronique,Cossy, Janine
supporting information, p. 5594 - 5597,4 (2012/12/12)
The stereoselective synthesis of conjugated trienes has been achieved from allylic alcohols and 1-iodo-1,3-dienes using Pd(OAc)2/AgOAc.
EPOXYEICOSATRIENOIC ACID ANALOGS AND METHODS OF MAKING AND USING THE SAME
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Page/Page column 77, (2012/10/18)
Compounds and compositions comprising epoxyeicosatrienoic acid (EET) analogs that act as EET agonists and are useful as medications in the treatment of drug-induced nephrotoxicity, hypertension and other related conditions. Methods of making and using the
Enantioselective synthesis of (10S)- and (10R)-methyl-anandamides
Nikas, Spyros P.,D'Souza, Marsha,Makriyannis, Alexandros
supporting information; experimental part, p. 6329 - 6337 (2012/09/08)
For the development of novel endocannabinoid templates with potential resistance to hydrolytic and oxidative metabolism, we are targeting the bis-allylic carbons of the arachidonoyl skeleton. Toward this end, we recently disclosed the synthesis and prelim
Total synthesis of (-)-dendrobine
Kreis, Lukas M.,Carreira, Erick M.
supporting information; experimental part, p. 3436 - 3439 (2012/06/30)
Cascading to alkaloids: An 18-step total synthesis of (-)-dendrobine is based on a reaction cascade with a key amine group (see scheme, Bn=benzyl). The amine is the initiator of the cascade and provides an efficient method for installing the stereocenters at C11 and C3. The overall transformation occurs stereoselectively only when the conversion is carried out without the isolation of intermediates. Copyright
DBU-promoted facile, chemoselective cleavage of acetylenic TMS group
Yeom, Chang-Eun,Mi, Jeong Kim,Choi, Whail,Kim, B. Moon
, p. 565 - 568 (2008/12/22)
Acetylenic trimethylsilyl (TMS) groups were efficiently removed using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). With either 1.0 or even 0.1 equivalents of DBU, smooth desilylation of various terminal acetylenic TMS groups was accomplished selectively in the presence of alkyl silyl ethers and other base-labile groups. Furthermore, more sterically hindered terminal acetylenic silyl groups such as TBDMS and TIPS remained intact under these conditions. Georg Thieme Verlag Stuttgart.
On the synthesis of pyrinodemin A. Part 1: The location of the olefin
Romeril, Stuart P.,Lee, Victor,Baldwin, Jack E.,Claridge, Timothy D.W.
, p. 1127 - 1140 (2007/10/03)
The elucidation of the structure of the cytotoxic marine sponge alkaloid pyrinodemin A by synthesis is described. Based on the 13C NMR spectra of three double bond positional isomers and the natural product, it is concluded the C14′-C15′ isomer
Total synthesis and biological evaluation of the protein phosphatase 2A inhibitor cytostatin and analogues
Bialy, Laurent,Waldmann, Herbert
, p. 2759 - 2780 (2007/10/03)
The total synthesis of the natural product cytostatin is described which inhibits protein phosphatase 2A. Cytostatin has anti-metastatic properties and induces apoptosis. On the basis of this synthesis the relative and absolute configuration of cytostatin could be assigned. Key structural elements of cytostatin are an α,β-unsaturated lactone group and a side chain embodying a phosphate and a rather unstable (Z,Z,E)-triene subunit. In addition, the natural product carries six stereocenters. For the construction of the stereocenters reagent-controlled transformations were used in order to ensure maximum stereochemical flexibility. The Evans syn-aldol reaction was chosen to establish the stereochemistry at C-4, C-5, C-9 and C-10; C-6 was introduced by means of the Evans asymmetric alkylation. In all cases the same chiral auxiliary was employed as stereodirecting group. The stereocenter at C-11 was established by an asymmetric reduction using CBS-oxazaborolidine. Temporary protection of the phosphate group was achieved best by using the base-labile 9-fluorenylmethyl group, which could be cleanly cleaved by an excess of triethylamine; this reaction yielded analytically pure phosphates after a simple aqueous work-up. The (Z,Z,E)-triene embodied in cytostatin was synthesized by means of a Stille coupling as key transformation. The synthesis sequence established in this way readily gave access to a series of analogues with simplified structure. Initial biological testing of these analogues proved that the α,β-unsaturated lactone, the C-11-hydroxy group and a fully deprotected phosphate moiety at C-9 are essential for the PP2A-inhibitory activity of cytostatin. The rather unstable triene moiety in the side chain can be replaced by other lipophilic residues with only moderate decrease of biological activity. Other phosphatases, that is, PP1, VHR, PTP1B, CD45, were not inhibited by cytostatin or any of the analogues, demonstrating the high selectivity of this compound. These findings will be useful for the design and synthesis of cytostatin-derived chemical tools for the study of biological processes influenced by PP2A.
Aminoalkoxybenzoyl-benzofuran or benzothiophene derivatives, method of preparing same and compositions containing same
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Page 27, (2010/02/03)
Benzothiophenes and related compounds of formula (1), wherein A, B, Z are independently —CH═, —CR4═ or ═N—; X is —S—, —O—, —NH—, —NR2, —CH2—CH2—, CH2—CH2—CH2—, —CH2—O—; —OCH2—, —CH2—S—, —CO—, —SCH2—. —N═CR2— or —R2C═N—; Y is optionally substituted phenyl, alkyl, cycloalkyl, cycloalkenyl, heterocycle or bicyclic ring system; D is —CO—, CR2R3—, —CONH—, —NHCO—, —CR2(OH)—, —CONR2, NOR1 CH—NO2 N—CN —NR2—CO—, —C—, —C—, —C—; E is a single bond, optionally substituted phenyl, heterocycle; Z1 is —(CH2)p W(CH2)q—, —O(CH2)p CR5R6— or —O(CH2)p W(CH2)q; G is —NR7R8, (a), (b), (c), a 5- or 6-membered saturated, unsaturated or partially unsaturated and optionally substituted heterocycle or a bicyclic amine containing 5 to 12 carbon atoms either bridged or fused and optionally substituted and R is halogen, —NR2R3, —NHCOR2, —NHSO2R2, —CR2R3OH, —CONR2R3, —SO2NR2R3, OH, —OR1, —O—COR1; are estrogen agonists which are useful for treating syndromes and diseases caused by estrogen deficiency.
