- Novel method for the synthesis of lenvatinib using 4-nitrophenyl cyclopropylcarbamate and their pharmaceutical salts
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4-Nitrophenyl cyclopropylcarbamate was deployed as a novel synthon for the synthesis of anticancer drug lenvatinib. 4-Nitrophenyl cyclopropylcarbamate was prepared by the reaction of 4-nitrophenyl chloroformate and cyclopropyl amine in acetonitrile at room temperature. Furthermore, lenvatinib was synthesized by reacting 4-(4-amino-3-chlorophenoxy)-7-methoxyquinoline-6-carboxamide with 4-nitrophenyl cyclopropylcarbamate in good yields. Apart from the synthesis of lenvatinib, citrate, phosphate, malate and oxalate salts of?lenvatinib were also reported in good yields.
- Sadineni, Ravi Kumar,Rapolu, Rajesh Kumar,Raju, V. V. N. K. V. Prasada,Srinivasu,Malladi, Sireesha,Mulakayala, Naveen
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p. 1475 - 1483
(2020/11/05)
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- A safe and efficient route for the preparation of nitro-, dinitro-, and trinitrophenyl chloroformates
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A safe and simple method has been developed for synthesis of chloroformates derived from 2-nitrophenol, 4-nitrophenol, 2,4-dinitrophenol, 2,4,6-trinitrophenol, and pentafluorophenol, the yields being in the range of 72-96%. The method is based on a heterogeneous reaction of the substituted phenol with phosgene dissolved in dichloromethane catalyzed with solid anhydrous potassium carbonate. The synthesis of 2,4,6-trinitrophenyl chloroformate takes place only in the presence of a phase-transfer catalyst, in this case the easily recovered α,ω-dimethoxy poly(ethylene glycol) (PEG; M = 2kDa). The only waste products of the suggested synthesis of the mentioned esters are sodium chloride and potassium chloride. The method markedly reduces the explosion risk connected with drying and handling of salts of mono-, di-, and trinitrophenols and is much more environmentally friendly than the currently used methods. Copyright
- Sedlak, Milos,Pejchal, Vladimir,Imramovsky, Ales,Hanusek, Jiri
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supporting information
p. 2365 - 2369
(2013/07/26)
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- Synthesis and biological activity evaluation of cytidine-5′-deoxy-5- fluoro-N-[(alkoxy/aryloxy)] carbonyl-cyclic 2′,3′-carbonates
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Capecitabine, an oral prodrug of 5-FU was developed to improve the tumor selectivity and tolerability. To enhance the efficacy of capacitabine, a series of 5′-deoxy-5-fluorocytidine derivatives 5a-e were synthesized. In the present study, we investigated antitumor activity of 5′-deoxy-5- fluorocytidine derivatives both in vivo and in vitro methods. Title compounds were non-mutagenic to Salmonella typhimurium tester strain in Ames test. Compounds 5d and 5e are potent to inhibit the proliferation of NCI-69, PZ-HPV-7, MCF-7 and HeLa cells in MTT assay. In particular, 5d and 5e showed potent antitumor activities against L1210 leukemia cell line. Collectively, these findings suggest that 5d and 5e are more potent anti-cancer compounds than capecitabine.
- Jhansi Rani,Raghavendra,Kishore,Nanda Kumar,Hema Kumar,Jagadeeswarareddy
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experimental part
p. 690 - 696
(2012/09/08)
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- (Cyclopentadienyl)ruthenium-catalyzed regio- and enantioselective decarboxylative allylic etherification of allyl aryl and alkyl carbonates
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(Cyclopentadienyl)tris(acetonitrile)ruthenium hexafluorophosphate {[CpRu(NCMe)3][PF6] or (cyclopentadienyl) (I·6-naphthalene)ruthenium hexafluorophosphate {[CpRu(I·6-naphthalene)][PF6]} in combination with a pyridine oxazoline ligand efficiently catalyze the decarboxylative allylic rearrangement of allyl aryl carbonates. Good levels of regio- and enantioselectivity are obtained. Starting from enantioenriched secondary carbonates, the reaction is stereospecific and the corresponding allylic ethers are obtained with net retention of configuration. An intermolecular version of this transformation was also developed using allyl alkyl carbonates as substrates. Conditions were found to obtain the corresponding products with similar selectivity as in the intramolecular process. Through the use of a hemi-labile hexacoordinated phosphate counterion, a zwitterionic air- and moisture-stable chiral ruthenium complex was synthesized and used in the enantioselective etherification reactions. This highly lipophilic metal complex can be recovered and efficiently reused in subsequent catalysis runs. Copyright
- Austeri, Martina,Linder, David,Lacour, Jerome
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experimental part
p. 3339 - 3347
(2011/02/23)
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- One-pot radiosynthesis of [13N]urea and [13N] carbamate using no-carrier-added [13N]NH3
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The aim of this study was to develop a practical labeling method of [ 13N]ligands using no-carrier-added [13N]NH3 with high specific activity. [13N]urea analogues [13N]1a and [13N]2a or [13N]carbamate [13N]3a were synthesized by reacting isocyanate 5a, carbamoyl chloride 6a or chloroformate 7a with [13N]NH3. The precursors 5a-7a were prepared by treating amines 8a and 9a and alcohol 10a with triphosgene in situ. These reaction mixtures were not purified and were used directly for [ 13N]ammonolysis, respectively. Using the one-pot method, we synthesized [13N]carbamazepine ([13N]4), a putative positron emission tomography ligand for brain imaging. Copyright
- Kumata, Katsushi,Takei, Makoto,Ogawa, Masanao,Kato, Koichi,Suzuki, Kazutoshi,Zhang, Ming-Rong
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experimental part
p. 166 - 172
(2010/07/02)
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- DIARYLAMINE-CONTAINING COMPOUNDS AND COMPOSITIONS, AND THEIR USE AS MODULATORS OF C-KIT RECEPTORS
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Described herein are compounds that include a diarylamine structural feature. Also described herein are methods for making such compounds, methods for using such compounds to modulate the activity of c-kit receptors, and pharmaceutical compositions and medicaments comprising such compounds. Also described herein are methods of using such compounds, pharmaceutical compositions and medicaments to treat and/or prevent and/or inhibit and/or ameliorate the pathology and/or symptomology diseases or conditions associated with the activity of c-kit receptors.
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Page/Page column 171
(2008/06/13)
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- Synthesis of Anthropomorphic Molecules: The NanoPutians
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Described here are the synthetic details en route to an array of 2-nm-tall anthropomorphic molecules in monomeric, dimeric, and polymeric form. These anthropomorphic figures are called, as a class, NanoPutians. Using tools of chemical synthesis, the ultimate in designed miniaturization can be attained while preparing the most widely recognized structures: those that resemble humans.
- Chanteau, Stephanie H.,Tour, James M.
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p. 8750 - 8766
(2007/10/03)
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- Tricyclic triazolobenzazepine derivatives, process for producing the same, and antiallergic
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Tricyclic triazolobenzazepine derivatives in the form or a prodrug are provided. The compounds according to the present invention are those represented by formula (I) and pharmacologically acceptable salts and solvates thereof. The compounds are useful as antiallergic agents and exhibit excellent bioavailability. wherein R1 represents hydrogen, OH, alkyl or phenyl alkyl,R2, R3, R4, and R5 represent hydrogen, halogen, optionally protected hydroxyl, formyl, optionally substituted alkyl, alkenyl, alkoxy or the like, andQ represents a group selected from the following groups (i) to (iv), halogen, or alkoxy:
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- Hirudin/polyalkylene glycol conjugates and hirudin muteins
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Hirudin/polyalkylene glycol derivatives of the formula and hirudin muteins and the preparation thereof are described. The compounds are suitable for controlling diseases.
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- Prodrugs for enzyme mediated activation
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Enzymatically clearable prodrugs with reduced Michaelis-Menten constant (Km) are described.
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- Glycosylated prodrugs, their method of preparation and their uses
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Glycosylated prodrugs, a preparation method therefor, and their use with tumor-specific immunoenzymatic conjugates for the treatment of cancer, are described. These anthracycline prodrugs have formula (I). STR1
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- A convenient method for the synthesis of activated N-methylcarbamates
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An investigation of methods to efficiently prepare activated N-methylcarbamates is reported. N-(Methylcarbamoyloxy)succinimide (3a), aryl N-methylcarbamates 3b-d and 2,2,2-trifluoro-1-(trifluoromethyl)ethyl N-methylcarbamate (3e) have been prepared in 70-80% yields from the corresponding chloroformates 5a-e, which were prepared as crystalline solids by the condensation of trichloromethylchloroformate (1) or bis(trichloromethyl)carbonate (2) with hydroxy compounds 4a-e in high yields.
- Konakahara,Ozaki,Sato,Gold
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p. 103 - 106
(2007/10/02)
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- CHOLECYSTOKININ ANTAGONISTS
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Benzodiazepine analogs of the formula: STR1 are disclosed which are antagonists of gastrin and cholecystokinin (CCK).
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