35150-08-4Relevant articles and documents
Asymmetric synthesis of the central tryptophan residue of stephanotic acid
Bentley, David J.,Moody, Christopher J.
, p. 3545 - 3547 (2004)
The C-6 substituted tryptophan di- and tri-peptides 5 and 6, representing the tryptophan core of stephanotic acid, have been synthesized, the key steps being the formation of the phosphono-di- and tri-peptides 8 and 10 by a highly chemo-selective rhodium(II) catalyzed carbene N-H insertion reaction, their subsequent Horner-Wadsworth-Emmons reactions with N-Boc-6-bromoindole-3- carboxaldehyde, and the rhodium(I) catalyzed asymmetric hydrogenation of the resulting dehydro di- and tri-peptides.
Holzapfel-Meyers-Nicolaou modification of the Hantzsch thiazole synthesis
Merritt, Eleanor A.,Bagley, Mark C.
, p. 3535 - 3541 (2007)
Modified conditions for Hantzsch thiazole synthesis provides valine- and threonine-derived thiazoles without significant loss of optical purity. This two- or three-step procedure proceeds by the cyclocondensation of the corresponding thioamide under basic conditions, according to modified methods of Meyers and Holzapfel. The hydroxythiazoline intermediate is then dehydrated by treatment with trifluoroacetic anhydride-pyridine, followed by triethylamine, according to Nicolaou's procedure. Solvolysis of the trifluoroacetamide derivative produced in this process can be affected with sodium ethoxide in ethanol to give a reliable method for the stereoselective synthesis of functionalised thiazole building blocks in high yield. Georg Thieme Verlag Stuttgart.
Design, synthesis and cytotoxic evaluation of a library of oxadiazole-containing hybrids
Camacho, Cristián M.,Pizzio, Marianela G.,Roces, David L.,Boggián, Dora B.,Mata, Ernesto G.,Bellizzi, Yanina,Barrionuevo, Elizabeth,Blank, Viviana C.,Roguin, Leonor P.
, p. 29741 - 29751 (2021/10/07)
The development of hybrid compounds led to the discovery of new pharmacologically active agents for some of the most critical diseases, including cancer. Herein, we describe a new series of oxadiazole-containing structures designed by a molecular hybridiz
Development of new catalytic enantioselective formation of methylenelactam-based N,O-spirocyclic compounds via ring opening-asymmetric reclosure of hydroxylactams
Sengoku, Tetsuya,Miyoshi, Ayako,Tsuda, Tamaki,Inuzuka, Toshiyasu,Sakamoto, Masami,Takahashi, Masaki,Yoda, Hidemi
, (2020/05/18)
Catalytic enantioselective formation of methylenelactam-based N,O-spirocyclic compounds is developed. Hydroxylactams prepared from N-carbonyl phthalimides and β-amido functionalized allylboronates underwent ring opening-asymmetric reclosure in the presence of catalytic amounts of MgBr2 and a chiral aminophenol to afford the corresponding N,O-spirocyclic compounds in excellent yields and high enantioselectivities.
COMPOSITION COMPRISING OXALAMIDE GELATORS AND VEGETABLE OIL
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Page/Page column 13, (2020/07/14)
The present invention relates to the composition with gelling properties comprising oxalamide gelators of Formula (I) and a vegetable oil. Uses of such composition in the food, cosmetic or pharmaceutical industry are disclosed.
Singlet Oxygen Photooxidation of Peptidic Oxazoles and Thiazoles
Manfrin, Alessandro,Borduas-Dedekind, Nadine,Lau, Kate,McNeill, Kristopher
, p. 2439 - 2447 (2019/02/26)
Oxazoles and thiazoles are commonly found moieties in nonribosomal peptides (NRPs) and ribosomally synthesized post-translationally modified peptides (RiPPs), which are important biomolecules present in the environment and in natural waters. From previous studies, they seem susceptible to oxidation by singlet oxygen (1O2); therefore, we designed and synthesized model oxazole- and thiazole-peptides and measured their1O2 bimolecular reaction rate constants, showing slow photooxidation under environmental conditions. We reasoned their stability through the electron-withdrawing effect of the carboxamide substituent. Reaction products were elucidated and support a reaction mechanism involving cycloaddition followed by a series of rearrangements. The first1O2 bimolecular reaction rate constant for a RiPP, the thiazole-containing peptide Aerucyclamide A, was measured and found in good agreement with the model peptide's rate constant, highlighting the potential of using model peptides to study the transformations of other environmentally relevant NRPs and RiPPs.
Novel Fubinaca/Rimonabant hybrids as endocannabinoid system modulators
Stefanucci, Azzurra,Macedonio, Giorgia,Dvorácskó, Szabolcs,T?mb?ly, Csaba,Mollica, Adriano
, p. 1595 - 1605 (2018/09/14)
The discovery of novel modulators of the cannabinoid system is a current topic in medicinal chemistry. In this paper, we report nine novel carboxamides designed as hybrids of Fubinaca family compounds and Rimonabant. These hybrids were obtained by linking the 1-benzyl-2,5-dichloroindazole-3-carboxylic acid to different amino acids bearing a hydrophobic side chain and three different C-terminus. The new chemical entities were tested in vitro to evaluate their bioactivity by means of receptor binding assays and [35S]GTPγS stimulation assays to reveal their affinity and potency. We found that all compounds were able to bind to the cannabinoid receptors in the low nanomolar range with a marked selectivity towards the CB1 cannabinoid receptor. Some of them are full agonists, whereas the others act as partial agonists. These molecules could be potentially used as anti-obesity agents, antiemetic and analgesics.
Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1S,2R)-tranylcypromine
Ezawa, Tetsuya,Kawashima, Yuya,Noguchi, Takuya,Jung, Seunghee,Imai, Nobuyuki
, p. 1690 - 1699 (2017/11/14)
Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement.
Total Synthesis of the Cyclic Dodecapeptides Wewakazole and Wewakazole B
Inman, Martyn,Dexter, Hannah L.,Moody, Christopher J.
supporting information, p. 3454 - 3457 (2017/07/15)
The cyclic dodecapeptides wewakazole and wewakazole B have been synthesized by a divergent strategy via a common tris-proline containing oxazole octapeptide and two separate bis-oxazole containing tetrapeptide units, followed by peptide coupling and macro
RITA Mimics: Synthesis and Mechanistic Evaluation of Asymmetric Linked Trithiazoles
Pietkiewicz, Adrian L.,Zhang, Yuqi,Rahimi, Marwa N.,Stramandinoli, Michael,Teusner, Matthew,McAlpine, Shelli R.
supporting information, p. 401 - 406 (2017/04/21)
The established cytotoxic agent RITA contains a thiophene-furan-thiophene backbone and two terminal alcohol groups. Herein we investigate the effect of using thiazoles as the backbone in RITA-like molecules and modifying the terminal groups of these trithiazoles, thereby generating 41 unique structures. Incorporating side chains with varied steric bulk allowed us to investigate how size and a stereocenter impacted biological activity. Subjecting compounds to growth inhibition assays on HCT-116 cells showed that the most potent compounds 7d, 7e, and 7h had GI50 values of 4.4, 4.4, and 3.4 μM, respectively, versus RITA (GI50 of 800 nM). Analysis of these compounds in apoptosis assays proved that 7d, 7e, and 7h were as effective as RITA at inducing apoptosis. Evaluating the impact of 7h on proteins targeted by RITA (p53, c-Myc, and Mcl-1) indicated that it acts via a different mechanism of action to that of RITA. RITA suppressed Mcl-1 protein via p53, whereas compound 7h suppressed Mcl-1 expression via an alternative mechanism independent of p53.
