85846-38-4Relevant articles and documents
Asymmetric synthesis of the C15-C32 fragment of alotamide and determination of the relative stereochemistry
Shi, Hao-Yun,Xie, Yang,Hu, Pei,Guo, Zi-Qiong,Lu, Yi-Hong,Gao, Yu,Huang, Cheng-Gang
, (2018)
Alotamide is a cyclic depsipetide isolated from a marine cyanobacterium and possesses a unique activation of calcium influx in murine cerebrocortical neurons (EC50 4.18 μM). Due to its limited source, the three stereocenters (C19, C28, and C30) in its polyketide fragment remain undetermined. In this study, the first asymmetric synthesis of its polyketide fragment was achieved. Four relative possible diastereomers were constructed with a boron-mediated enantioselective aldol reaction and Julia-Kocienski olefination as the key steps. Comparison of 13C NMR spectra revealed the relative structure of fragment C15-C32 of alotamide.
2-AMINO-1,3,4-THIADIAZINE AND 2-AMINO-1,3,4-OXADIAZINE BASED ANTIFUNGAL AGENTS
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Page/Page column 74, (2017/02/09)
The invention provides a compound which is a diazine of formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt thereof, for use as an antifungal agent: (I) wherein X, N', C', A and E are as defined herein. The invention also provides a compound of Formula (I) as defined herein.
Synthesis and Cytotoxicity Evaluation of C4- and C5-Modified Analogues of the α,β-Unsaturated Lactone of Pironetin
Huang, David S.,Wong, Henry L.,Georg, Gunda I.
supporting information, p. 520 - 528 (2017/04/10)
Pironetin is a natural product with potent antiproliferative activity that forms a covalent adduct with α-tubulin via conjugate addition into the natural product's α,β-unsaturated lactone. Although pironetin's α,β-unsaturated lactone is involved in its binding to tubulin, the structure–activity relationship at different positions of the lactone have not been thoroughly evaluated. For a systematic evaluation of the structure–activity relationships at the C4 and C5 positions of the α,β-unsaturated lactone of pironetin, twelve analogues of the natural product were prepared by total synthesis. Modifying the stereochemistry at the C4 and/or C5 positions of the α,β-unsaturated lactone of pironetin resulted in loss of antiproliferative activity in OVCAR5 ovarian cancer cells. While changing the C4 ethyl substituent with groups such as methyl, propyl, cyclopropyl, and isobutyl were tolerated, groups with larger steric properties such as an isopropyl and benzyl groups were not.
Stereoselective synthesis of 1,3-anti diols by an Ipc-mediated domino aldol-coupling/reduction sequence
Dieckmann, Michael,Menche, Dirk
supporting information, p. 228 - 231 (2013/03/28)
A novel domino process for 1,3-anti diol synthesis by the union of a methyl ketone with an aldehyde is described. The operationally simple procedure is based on an Ipc-boron-aldol coupling and subsequent Ipc-mediated reduction of the intermediate β-hydrox
A practical method for p -methoxybenzylation of hydroxy groups using 2,4,6-tris(p -methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM)
Yamada, Kohei,Fujita, Hikaru,Kitamura, Masanori,Kunishima, Munetaka
, p. 2989 - 2997 (2013/11/06)
A new acid-catalyzed p-methoxybenzylating reagent, 2,4,6-tris(p- methoxybenzyloxy)-1,3,5-triazine (TriBOT-PM), has been developed. The reaction of acid- and alkali-labile alcohols with TriBOT-PM in the presence of a catalytic amount of various acids (TfOH, BF3·OEt2, CSA, etc.) afforded the corresponding p-methoxybenzyl ethers in good yields. Since TriBOT-PM is an air-stable crystalline solid and can be prepared from inexpensive materials, i.e. cyanuric chloride and anisyl alcohol, this route is of practical use. Georg Thieme Verlag Stuttgart, New York.
Benzylation of hydroxy groups with tertiary amine as a base
Gathirwa, Jeremiah W.,Maki, Toshihide
experimental part, p. 370 - 375 (2012/01/14)
The benzylation of hydroxy groups in the presence of tertiary amines is described. A mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields in the presence of diisopropylethylamine. The importance of solventless conditions was observed. The reaction showed high tolerance to many functional groups including benzoate, even at a reaction temperature of 150 °C. Sodium iodide was found to be an efficient catalyst to accelerate the reaction.
Modular total synthesis of archazolid A and B
Menche, Dirk,Hassfeld, Jorma,Li, Jun,Mayer, Kerstin,Rudolph, Sven
supporting information; experimental part, p. 7220 - 7229 (2010/02/17)
(Chemical Equation Presented) A modular total synthesis of the potent V-ATPase inhibitors archazolid A and B is reported. The convergent preparation was accomplished by late-stage diversification of joint intermediates. Key synthetic steps involve asymmetric boron-mediated aldol reactions, two consecutive Still-Gennari olefinations to set the characteristic (Z,Z)-diene system, a Brown crotyboration, and a diastereo-selective aldol condensation of highly elaborate intermediates. For macrocyclization, both an HWE reaction and a Heck coupling were successfully employed to close the 24-membered macrolactone. During the synthetic campaign, a generally useful protocol for an E-selective Heck reaction of nonactivated alkenes and a method for the direct nucleophilic displacement of the Abiko-Masamune auxiliary with sterically hindered nucleophiles were developed. The expedient and flexible strategy will enable further SAR studies of the archazolids and more detailed evaluations of target-inhibitor interactions. 2009 American Chemical Society.
Evaluating the potential of Vacuolar ATPase inhibitors as anticancer agents and multigram synthesis of the potent salicylihalamide analog saliphenylhalamide
Lebreton, Sylvain,Jaunbergs, Janis,Roth, Michael G.,Ferguson, Deborah A.,De Brabander, Jef K.
scheme or table, p. 5879 - 5883 (2009/06/25)
The natural product salicylihalamide is a potent inhibitor of the Vacuolar ATPase (V-ATPase), a potential target for antitumor chemotherapy. We generated salicylihalamide-resistant tumor cell lines typified by an overexpansion of lysosomal organelles. We also found that many tumor cell lines upregulate tissue-specific plasmalemmal V-ATPases, and hypothesize that tumors that derive their energy from glycolysis rely on these isoforms to maintain a neutral cytosolic pH. To further validate the potential of V-ATPase inhibitors as leads for cancer chemotherapy, we developed a multigram synthesis of the potent salicylihalamide analog saliphenylhalamide.
Total synthesis of archazolid A
Menche, Dirk,Hassfeld, Jorma,Li, Jun,Rudolph, Sven
, p. 6100 - 6101 (2008/02/08)
The archazolids are complex polyketides isolated from the myxobacterium Archangium gephyra and are potent inhibitors of vacuolar type ATPases. Herein, we report the first total synthesis of archazolid A, which establishes unequivocally the relative and ab
Rhodium-catalyzed addition of alcohols to terminal enones
Farnworth, Marc V.,Cross, Michael J.,Louie, Janis
, p. 7441 - 7443 (2007/10/03)
[Rh(COD)(OMe)]2 was found to catalyze the addition of aliphatic and aromatic alcohols with terminal enones to afford β-alkoxyketones in high yields.
