83553-49-5Relevant academic research and scientific papers
A concise and efficient route to the total synthesis of bacillamide A and its analogues
Kumar, Sunil,Aggarwal, Ranjana
, p. 354 - 361 (2018/07/05)
The synthesis of bacillamide A, a tryptamide alkaloid of marine origin, and its analogues from L-cysteine ethyl ester hydrochloride through an efficient and convergent synthetic approach is described in this work. The present two-step protocol involves th
Solvent-free synthesis of bacillamide analogues as novel cytotoxic and anti-inflammatory agents
Kumar, Sunil,Aggarwal, Ranjana,Kumar, Virender,Sadana, Rachna,Patel, Bhumi,Kaushik, Pawan,Kaushik, Dhirender
, p. 718 - 726 (2016/08/15)
Synthesis of fourteen analogues of bacillamide, a bioactive tryptamide alkaloid of marine origin, has been accomplished through a highly efficient convergent route. The present solvent-free protocol involves the formation of thiazole ring in the initial step followed by amide coupling between substituted ethyl 2-alkyl/aryl/heteroaryl/amino/aminoarylthiazole-4-carboxylates and tryptamine in presence of 2-hydroxy-4,6-dimethylpyrimidine, a solid phase catalyst to yield N-[2-(1H-indol-3-yl)ethyl]-2-alkyl/aryl/heteroaryl/amino/aminoarylthiazole-4-carboxamides as bacillamide analogues having structural variation at position-2 of thiazole ring. Bacillamide and its analogues were evaluated for their cytotoxic activity against three cancer cell lines (HCT-116, MDA-MD-231 and JURKAT cell lines) using colorimetric cell proliferation assay. Compounds 17a and 17b exhibited potent anti-cell proliferation activity with IC50values in the range of ～3.0?μM and ～0.1–0.6?μM, respectively against these cell lines. Preliminary mechanism of action studies indicates that these compounds initiate caspase dependent apoptosis. Also, compounds 16d, 16f, 17a and 17d exhibited excellent anti-inflammatory activity comparable to well-known NSAID indomethacin and better to bacillamide, when evaluated using carrageenan induced rat hind paw oedema method.
Synthesis and Biological Investigation of Oxazole Hydroxamates as Highly Selective Histone Deacetylase 6 (HDAC6) Inhibitors
Senger, Johanna,Melesina, Jelena,Marek, Martin,Romier, Christophe,Oehme, Ina,Witt, Olaf,Sippl, Wolfgang,Jung, Manfred
supporting information, p. 1545 - 1555 (2016/03/08)
Histone deacetylase 6 (HDAC6) catalyzes the removal of an acetyl group from lysine residues of several non-histone proteins. Here we report the preparation of thiazole-, oxazole-, and oxadiazole-containing biarylhydroxamic acids by a short synthetic proce
Synthesis of (4R,5S)-melithiazols F and I
Takayama, Hiroyuki,Kato, Keisuke,Akita, Hiroyuki
, p. 644 - 649 (2007/10/03)
Palladium-catalyzed cyclization-methoxycarbonylation of (2R,3S)-3-methylpenta-4-yne-1,2-diol (8) derived from the (2R,3S)-epoxybutanoate 7 followed by methylation gave the tetrahydro-2-furylidene acetate (-)-9, which was converted into the left-half aldehyde (+)-4. A Wittig reaction between (+)-4 and the phosphoranylide derived from the bithiazole-type phosphonium iodide 5 using lithium bis(trimethylsilyl)-amide afforded (+)-(4R,5S)- melithiazol F (1), whose spectroscopic data were identical with those of the natural product 1. Moreover, the synthesis of (+)-(4R,5S)-melithiazol I (2), was achieved by the same synthetic strategy as that of (+)-(4R,5S)-melithiazol F (1). The antifungal activity of the synthetic melithiazols F (1) and I (2) against the phytopathogenic fungus, Phytophthora capsici, was evaluated by using a paper disc assay method. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
A catch-and-release strategy for the combinatorial synthesis of 4-acylamino-1,3-thiazoles as potential CDK5 inhibitors
Larsen, Scott D.,Stachew, Carl F.,Clare, Paula M.,Cubbage, Jerry W.,Leach, Karen L.
, p. 3491 - 3495 (2007/10/03)
Two-dimensional libraries of 4-acylamino-1,3-thiazoles 9 were prepared via Curtius rearrangement of 1,3-thiazole-4-carbonyl azides 6, trapping of the intermediate isocyanates with oxime resin, and thermal regeneration of the isocyanates from the washed resin in the presence of nucleophiles. Several compounds proved to be selective inhibitors of CDK5/p25 versus the closely homologous CDK2/cyclin A enzyme, with the best analogue (43) possessing over 100-fold selectivity.
Synthesis of 2-substituted-4-carbethoxythiazoles
Kim, Hong-Seok,Kwon, Il-Cheon,Kim, Oh-Hwoan
, p. 937 - 940 (2007/10/03)
In the presence of boron trifluoride etherate, aryl and alkylthioamides react with ethyl diazopyruvate to give high yields of corresponding thiazoles.
Novel analogues of tiazofurin by Lawesson reagent effected cyclization
Golankiewicz,Januszczyk
, p. 313 - 316 (2007/10/02)
2-Benzylthiazole-4-carboxamide 4 and 5-(β-D-ribofuranosylamino) thiazole-4-carboxamide 10 were synthesized from phenylacetylamino- and formylamino cyanoacetic acid esters 1a and 1b, respectively. The ribosylation reaction leading to 10 gave rise also to i
Heterocyclic alcohols and their derivatives
-
, (2008/06/13)
Novel heterocyclic compounds of the formula STR1 wherein X is selected from the group consisting of chlorine, bromine, iodine and --OH, W is selected from the group consisting of hydrogen and --CN, Z is selected from the group consisting of --CH2/su
