21714-25-0Relevant academic research and scientific papers
Demethylative Lactonization Provides a Shortcut to High-Yielding Syntheses of Lamellarins
De Koning, Charles B.,Klintworth, Robin,Michael, Joseph P.
, (2020/01/31)
Modular gram-scale syntheses of the trimethyl ethers of lamellarins G (6) and D (7) were achieved from readily accessible precursors in the highest overall yields reported to date (6, six steps, 82%; 7, seven steps, 86%). A novel demethylative lactonizati
Practical Decagram-Scale Synthesis of a Lamellarin Analogue and Deprotection of Lamellarin Isopropyl Ethers
Klintworth, Robin,de Koning, Charles B.,Michael, Joseph P.
, p. 3860 - 3871 (2020/06/17)
Modular syntheses of naturally occurring lamellarin ε (5) and the synthetic analogue dehydrolamellarin J (6), both of them promising lead candidates for anticancer activity, were accomplished in high overall yields. Key steps in these routes are a late-st
A novel one-pot synthesis of isothiocyanates and cyanamides from dithiocarbamate salts using environmentally benign reagent tetrapropylammonium tribromide
Kuotsu, Neivotsonuo Bernadette,Jamir, Latonglila,Phucho, Tovishe,Sinha, Upasana Bora
, p. 832 - 841 (2018/01/17)
A highly efficient and simple protocol for the synthesis of isothiocyanates and cyanamides from their respective amines in the presence of a mild, efficient, and non-toxic reagent tetrapropylammonium tribromide is described. High environmental acceptability of the reagents, cost effectiveness and high yields are the important attributes of this methodology.
The role of 5-arylalkylamino- and 5-piperazino- moieties on the 7-aminopyrazolo[4,3-d]pyrimidine core in affecting adenosine A1 and A2A receptor affinity and selectivity profiles
Squarcialupi, Lucia,Betti, Marco,Catarzi, Daniela,Varano, Flavia,Falsini, Matteo,Ravani, Annalisa,Pasquini, Silvia,Vincenzi, Fabrizio,Salmaso, Veronica,Sturlese, Mattia,Varani, Katia,Moro, Stefano,Colotta, Vittoria
, p. 248 - 263 (2017/11/10)
New 7-amino-2-phenylpyrazolo[4,3-d]pyrimidine derivatives, substituted at the 5-position with aryl(alkyl)amino- and 4-substituted-piperazin-1-yl- moieties, were synthesized with the aim of targeting human (h) adenosine A1 and/or A2A receptor subtypes. On the whole, the novel derivatives 1–24 shared scarce or no affinities for the off-target hA2B and hA3 ARs. The 5-(4-hydroxyphenethylamino)- derivative 12 showed both good affinity (Ki = 150 nM) and the best selectivity for the hA2A AR while the 5-benzylamino-substituted 5 displayed the best combined hA2A (Ki = 123 nM) and A1 AR affinity (Ki = 25 nM). The 5-phenethylamino moiety (compound 6) achieved nanomolar affinity (Ki = 11 nM) and good selectivity for the hA1 AR. The 5-(N4-substituted-piperazin-1-yl) derivatives 15–24 bind the hA1 AR subtype with affinities falling in the high nanomolar range. A structure-based molecular modeling study was conducted to rationalize the experimental binding data from a molecular point of view using both molecular docking studies and Interaction Energy Fingerprints (IEFs) analysis. (Figure presented.).
The synthesis of sulforaphane analogues and their protection effect against cisplatin induced cytotoxicity in kidney cells
Kim, Taejung,Kim, Young-Joo,Han, Im-Ho,Lee, Dahae,Ham, Jungyeob,Kang, Ki Sung,Lee, Jae Wook
supporting information, p. 62 - 66 (2015/02/19)
A series of sulforaphane analogues were synthesized with various amines by treatment of carbon disulfide followed by Boc2O and DMAP. These synthesized sulforaphane analogues were tested on cisplatin treated cultured LLC-PK1 kidney cell line. Among these analogues, several compounds including SF5 show a potent effect on kidney cell protection assay at the concentration of 2.5 μM. Further studies with compound SF5 revealed that the kidney cell protection effect was related by inhibiting the apoptosis pathway through JNK-p53-caspase apoptotic cascade. Compound SF5 may be considered as a promising candidate for the development of new kidney protection agent against drug induced acute kidney disease.
Efficient preparation of isothiocyanates from dithiocarbamates using bromineless brominating reagent
Yella, Ramesh,Ghosh, Harisadhan,Murru, Siva,Sahoo, Santosh K.,Patel, Bhisma K.
experimental part, p. 2083 - 2096 (2010/08/19)
For the first time, the crystal structure of a ditribromide reagent 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) has been determined. Utilizing this thiophilic bromineless brominating agent EDPBT, highly useful synthetic intermediates (alkyl and aryl isothiocyanates) have been achieved directly from dithiocarbamates. EDPBT can be easily prepared from readily available reagents. It has been used as a thiophilic reagent, and its thiophilicity dominates over its brominating ability for substrates amenable to bromination. This is a sustainable process for the preparation of isothiocyantes because the spent reagent can be recovered, regenerated, and reused. Copyright Taylor & Francis Group, LLC.
A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine
Nath, Jayashree,Patel, Bhisma K.,Jamir, Latonglila,Sinha, Upasana Bora,Satyanarayana
experimental part, p. 1503 - 1506 (2010/05/18)
An efficient one-pot method for the synthesis of cyanamides from dithiocarbamate salts via a double desulfurization strategy using molecular iodine is disclosed. Dithiocarbamates, by the action of iodine yield isothiocyanates in situ, which on treatment with aqueous NH3 give thioureas. The thioureas so generated undergo further oxidative desulfurization with I2 giving corresponding cyanamides in good yields. Environmental benignity, cost effectiveness and high yields are the important attributes of this one pot procedure. The Royal Society of Chemistry 2009.
