155934-55-7Relevant articles and documents
A chiron approach to the total synthesis of cytotoxic (+)-muricatacin and (+)-5-epi-muricatacin from d-ribose
Ghosal, Partha,Kumar, Vikas,Shaw, Arun K.
, p. 41 - 44 (2010)
A chiron approach strategy toward the total synthesis of (+)-muricatacin and (+)-5-epi-muricatacin starting from commercially available and inexpensive d-ribose through the key intermediate (S)-5-((R)-1-hydroxyallyl)furan-2(5H)-one has been disclosed.
A short alternative preparation of the bengazoles polyol side-chain segment
Gallos, John K.,Stathakis, Christos I.,Salapassidou, Maria J.,Grammatoglou, Constantinos E.,Koumbis, Alexandros E.
, p. 744 - 748 (2007)
A new short and efficient synthesis of the bengazoles side chain is reported using a sequential Grignard addition-hydroboration approach on a readily available d-ribose derivative.
Stereoselective Total Synthesis of Arundinolides A and B
Chang, Caizhu,Dong, Zhi-Bing,Du, Yuguo,Geng, Jialin,Liu, Jun,Liu, Yinxin
, p. 1576 - 1584 (2020)
The efficient and enantioselective syntheses of arundinolides A and B have been accomplished for the first time from chiral pool methyl-2,3- O -isopropylidene-β- d -ribofuranoside and d -ethyl lactate. The key features of the total synthesis are intramolecular crotonyl migration and NaBH 4 -CuCl catalyzed regioselective reduction and cross-metathesis reaction.
MEAYAMYCIN ANALOGUES AND METHODS OF USE
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Page/Page column 5, (2021/10/15)
Compounds according to formula (I), where R is as defined herein, have anti-cancer properties.
Total Synthesis of Meayamycin and O-Acyl Analogues
Boger, Dale L.,Chanda, Prem B.,Chowdari, Naidu S.,Gangwar, Sanjeev,Gartshore, Christopher,Momirov, Jelena,Sarkar, Anindya,Tadano, Shinji,Vite, Gregory D.,Zhang, Qian
, (2020/11/18)
A short, scalable total synthesis of meayamycin is described by an approach that entails a longest linear sequence of 12 steps (22 steps overall) from commercially available chiral pool materials (ethyl l-lactate, BocNH-Thr-OH, and d-ribose) and introduces the most straightforward preparation of the right-hand subunit detailed to date. The use of the approach in the divergent synthesis of a representative series of O-acyl analogues is exemplified.
A novel and environmental friendly synthetic route for hydroxypyrrolidines using zeolites
Fan,Chuah,Jaenicke, Stephan
, p. 103 - 114 (2018/12/13)
A critical step in the synthesis of the hydroxypyrrolidines, 1,4-dideoxy-1,4-imino-L-lyxitol and 1,4-dideoxy-1,4-imino-D-lyxitol, from the corresponding D-sugars is the synthesis of O-methyl 2,3-O-isopropylidenepentofuranoses. Instead of applying homogeneous catalysis process with conventional inorganic acid catalysts like HCl and HClO4, it was found that heterogeneous catalysis using zeolites could be used for the one-pot synthesis of O-methyl 2,3-O-isopropylidenepentofuranoses directly from D-sugars, MeOH and acetone at mild condition. The best catalyst was H-beta zeolite containing a Si/Al molar ratio of 150, where a yield of >83% was obtained. The overall yields of the five-step procedure to 1,4-dideoxy-1,4-imino-L-lyxitol and 1,4-dideoxy-1,4-imino-D-lyxitol were 57% and 50%, respectively. This synthetic procedure has several advantages such as competitive overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the zeolite catalyst can be easily recovered from the reaction mixture and reused with no loss of activity.
Synthesis of N-alkyl substituted iminosugars from D-ribose
Wang, Haibo,Pan, Yang,Tang, Qin,Zou, Wei,Shao, Huawu
supporting information, p. 73 - 75 (2017/10/26)
An effective and facile method for the synthesis of N-alkylated hydroxylpyrrolidine and hydroxylpiperidine is described. A number of N-alkyl substituted iminosugars were prepared using iodine-induced intramolecular cyclization of acyclic alkenylamines as key step.
Chiral approach to total synthesis of phytotoxic and related nonenolides: (Z)-isomer of (6S,7R,9R)-6,7-dihydroxy-9-propylnon-4-eno-9-lactone, herbarumin-III and their C-9 epimers
Maram, Lingaiah,Parigi, Raghavendar Reddy,Das, Biswanath
, p. 7135 - 7142 (2016/10/22)
A new and efficient strategy has been developed for the stereoselective total synthesis of nonenolides: (Z)-isomer of (6S,7R,9R)-6,7-dihydroxy-9-propylnon-4-eno-9-lactone, herbarumin-III and their C-9 epimers starting from D (?) ribose. The synthesis includes the coupling of the alcohol and acid fragments of the molecules, employing Yamaguchi esterification protocol followed by intramolecular ring closure metathesis. The method has efficiently constructed the 10-membered lactone skeleton of the compounds with proper stereogenic centers containing appropriate functionalities.
South (S)- and north (N)-methanocarba-7-deazaadenosine analogues as inhibitors of human adenosine kinase
Toti, Kiran S.,Osborne, Danielle,Ciancetta, Antonella,Boison, Detlev,Jacobson, Kenneth A.
supporting information, p. 6860 - 6877 (2016/08/05)
Adenosine kinase (AdK) inhibitors raise endogenous adenosine levels, particularly in disease states, and have potential for treatment of seizures, neurodegeneration, and inflammation. On the basis of the South (S) ribose conformation and molecular dynamics (MD) analysis of nucleoside inhibitors bound in AdK X-ray crystallographic structures, (S)- and North (N)-methanocarba (bicyclo[3.1.0]hexane) derivatives of known inhibitors were prepared and compared as human (h) AdK inhibitors. 5′-Hydroxy (34, MRS4202 (S); 55, MRS4380 (N)) and 5′-deoxy 38a (MRS4203 (S)) analogues, containing 7- and N6-NH phenyl groups in 7-deazaadenine, robustly inhibited AdK activity (IC50 ～ 100 nM), while the 5′-hydroxy derivative 30 lacking the phenyl substituents was weak. Docking in the hAdK X-ray structure and MD simulation suggested a mode of binding similar to 5′-deoxy-5-iodotubercidin and other known inhibitors. Thus, a structure-based design approach for further potency enhancement is possible. The potent AdK inhibitors in this study are ready to be further tested in animal models of epilepsy.
Identification of a cytotoxic molecule in heat-modified citrus pectin
Leclere, Lionel,Fransolet, Maude,Cambier, Pierre,El Bkassiny, Sandy,Tikad, Abdellatif,Dieu, Marc,Vincent, Stéphane P.,Van Cutsem, Pierre,Michiels, Carine
, p. 39 - 51 (2015/11/09)
Modified forms of citrus pectin possess anticancer properties. However, their mechanism of action and the structural features involved remain unclear. Here, we showed that citrus pectin modified by heat treatment displayed cytotoxic effects in cancer cells. A fractionation approach was used aiming to identify active molecules. Dialysis and ethanol precipitation followed by HPLC analysis evidenced that most of the activity was related to molecules with molecular weight corresponding to low degree of polymerization oligogalacturonic acid. Heat-treatment of galacturonic acid also generated cytotoxic molecules. Furthermore, heat-modified galacturonic acid and heat-fragmented pectin contained the same molecule that induced cell death when isolated by HPLC separation. Mass spectrometry analyses revealed that 4,5-dihydroxy-2-cyclopenten-1-one was one cytotoxic molecule present in heat-treated pectin. Finally, we synthesized the enantiopure (4R,5R)-4,5-dihydroxy-2-cyclopenten-1-one and demonstrated that this molecule was cytotoxic and induced a similar pattern of apoptotic-like features than heat-modified pectin.
