Category: 96929-05-4

Pena, Stella; Scarone, Laura; Manta, Eduardo; Stewart, Lindsay; Yardley, Vanessa; Croft, Simon; Serra, Gloria published the artcile< Synthesis of a Microcystis aeruginosa predicted metabolite with antimalarial activity>, Category: thiazole, the main research area is peptidomimetic synthesis Microcystis aeruginosa metabolite antimalarial agent; peptide coupling oxazole thiazole macrocyclization.

The synthesis of a Microcystis aeruginosa predicted metabolite analog of aerucyclamide B was performed. This hexacyclopeptide was obtained from three heterocyclic building blocks by a convergent macrocycle-assembly methodol. The compound exhibited good in vitro antiplasmodial activity (IC50: 0.18μM, K1, chloroquine-resistant strain).

Bioorganic & Medicinal Chemistry Letters published new progress about Antimalarials. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Category: thiazole.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Okumura, Kazuro; Ito, Akio; Saito, Hiroyuki; Nakamura, Yutaka; Shin, Chung-gi published the artcile< Dehydrooligopeptides. XIV. Syntheses of 2-[(Z)-1-aminoalken-1-yl]oxazole-4-carboxylic acid and the main common skeleton of thiostrepton peptide antibiotics A10255G and A10255J.>, Recommanded Product: Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is dehydrooligopeptide preparation thiostrepton peptide antibiotic intermediate.

Precursor (I) to title cyclopeptide antibiotics (II; R = Q1, Q2) is constructed from novel 2-[(Z)-1-amino-1-propen-1-yl]oxazole-4-carboxylic acids (III; R1 = Me, Me2CH, Ph; R2 = H, Me) and 2-(1-aminomethyl)- and 2[(S)-1-aminoethyl]thiazole-4-carboxylic acid residues.

Bulletin of the Chemical Society of Japan published new progress about Peptide analogs Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Recommanded Product: Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Pietkiewicz, Adrian L.; Zhang, Yuqi; Rahimi, Marwa N.; Stramandinoli, Michael; Teusner, Matthew; McAlpine, Shelli R. published the artcile< RITA Mimics: Synthesis and Mechanistic Evaluation of Asymmetric Linked Trithiazoles>, Related Products of 96929-05-4, the main research area is RITA mimic trithiazole preparation antitumor colorectal p53 cMyc Mcl1; Heterocycle; Mcl-1; RITA; antitumor; c-Myc; p53; thiazole.

The established cytotoxic agent RITA contains a thiophene-furan-thiophene backbone and two terminal alc. groups. Herein the authors investigate the effect of using thiazoles as the backbone in RITA-like mols. and modifying the terminal groups of these trithiazoles, thereby generating 41 unique structures. Incorporating side chains with varied steric bulk allowed the authors to investigate how size and a stereocenter impacted biol. activity. Subjecting compounds to growth inhibition assays on HCT-116 cells showed that the most potent compounds 7d (BocHN-D-Val-Thiazole-Thiazole-Thiazole-OEt), 7e (BocHN-L-Val-Thiazole-Thiazole-Thiazole-OEt), and 7h (BocHN-CHA-thiazole-thiazole-thiazole-OEt) had GIC50 values of 4.4, 4.4, and 3.4 μM, resp., vs. RITA (GIC50 of 800 nM). Anal. 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.

ACS Medicinal Chemistry Letters published new progress about Antiproliferative agents. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Related Products of 96929-05-4.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Shin, Chung-gi; Okumura, Kazuo; Ito, Akio; Nakamura, Yutaka published the artcile< Synthesis of a common main skeleton of thiostrepton peptide antibiotics, A 10255G and J>, Safety of Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is thiostrepton peptide antibiotic A 10255G; peptide thiostrepton antibiotic A 10255J.

The synthesis of protected, common main skeleton I (boc = Me3CO2C) of thiostrepton peptides, A10255G and J, containing a few kinds of unusual amino acids is described.

Chemistry Letters published new progress about 96929-05-4. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Safety of Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Houssin, Raymond; Lohez, Michele; Bernier, Jean Luc; Henichart, Jean Pierre published the artcile< A convenient method for the preparation of 2-(1-aminoalkyl)thiazole-4-carboxylic acids, key intermediates in the total synthesis of naturally occurring antitumor cyclopeptides>, Safety of Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is thiazolecarboxylic acid aminoalkyl; thiazolyl amino acid; thioamide amino cyclocondensation bromopyruvate.

A convenient synthesis of 2-(1-aminoalkyl)thiazole-4-carboxylic acids I (Boc = Me3CO2C; R = H, Me, Me2CH, Me2CHCH2, EtCHMe, PhCH2) involving a Hantzsch condensation of BocNHCHRC(S)NH2 (II) with Et bromopyruvate is reported. The intermediate thioamides II are obtained from the corresponding amides by action of a Lawesson’s type reagent. This procedure constitutes a new access to key intermediates useful in the total synthesis of antitumor cyclopeptides extracted from marine animals.

Journal of Organic Chemistry published new progress about Amino acids Role: SPN (Synthetic Preparation), PREP (Preparation). 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Safety of Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Li, Xianlin; Tu, Zhenchao; Li, Hua; Liu, Chunping; Li, Zheng; Sun, Qiao; Yao, Yiwu; Liu, Jinsong; Jiang, Sheng published the artcile< Biological evaluation of new largazole analogues: Alteration of macrocyclic scaffold with Click chemistry>, Product Details of C12H18N2O4S, the main research area is cyclic peptide design synthesis largazole HDAC inhibitor structure activity; mol docking largazole HDAC enzyme active site crystal structure; thiazole ester Corey Fuchs reaction cycloaddition Click chem macrocyclization; HDAC inhibitor; click chemistry; largazole; macrocycles; peptides.

We report the design, synthesis, and biol. evaluation of a new series of largazole analogs in which a 4-methylthiazoline moiety was replaced with a triazole and tetrazole ring, resp. Compound (I) bearing a tetrazole ring was identified to show much better selectivity for HDAC1 over HDAC9 than largazole (10-fold). This work could serve as a foundation for further exploration of selective HDAC inhibitors using a largazole mol. scaffold.

ACS Medicinal Chemistry Letters published new progress about Azide-alkyne 1,3-dipolar cycloaddition reaction. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Product Details of C12H18N2O4S.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Moody, Christopher J.; Bagley, Mark C. published the artcile< Total synthesis of (+)-nostocyclamide>, Application of C12H18N2O4S, the main research area is nostocyclamide macrocyclic peptide total synthesis.

The synthesis of (+)-nostocyclamide (I) from the oxazole II and thiazoles III (R = H, CHMe2; Boc = Me3CO2C) is described. The oxazole amino ester II was prepared from N-protected alaninamide using a rhodium(II) catalyzed N-H insertion reaction as a key step, and the thiazoles III were obtained using a modified Hantzsch reaction. The synthesis was completed in six further steps in which fragments II and III (R = CHMe2) were coupled using mixed anhydride methodol. to give a oxazole-thiazole intermediate, deprotection of which and coupling to III (R = H) gave a linear bis-thiazole oxazole intermediate. Macrocyclization using the pentafluorophenyl ester method gave (+)-nostocyclamide I. The synthesis confirms that the natural product is the (+)-enantiomer and has the (2S,12R) absolute configuration.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry published new progress about 96929-05-4. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Application of C12H18N2O4S.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Thompson, Robert E.; Jolliffe, Katrina A.; Payne, Richard J. published the artcile< Total Synthesis of Microcin B17 via a Fragment Condensation Approach>, Name: Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is microcin B17 total synthesis peptide fragment coupling.

The total synthesis of the 43 amino acid-containing antibacterial peptide Microcin B17 (MccB17) is described. The natural product was synthesized via a convergent approach from a heterocycle-derived peptide and peptide thioester fragments prepared via Fmoc-strategy solid-phase peptide synthesis (SPPS). Final assembly was achieved in an efficient manner using two Ag(I)-assisted peptide ligation reactions to afford MccB17 in excellent overall yield.

Organic Letters published new progress about Amino acids, N-[(fluorenylmethoxy)carbonyl] Role: RCT (Reactant), RACT (Reactant or Reagent). 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Name: Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Healy, Alan R.; Wernke, Kevin M.; Kim, Chung Sub; Lees, Nicholas R.; Crawford, Jason M.; Herzon, Seth B. published the artcile< Synthesis and reactivity of precolibactin 886>, COA of Formula: C12H18N2O4S, the main research area is synthesis precolibactin 886 nucleophilic cleavage.

The clb gene cluster encodes the biosynthesis of metabolites known as precolibactins and colibactins. The clb pathway is found in gut commensal Escherichia coli, and clb metabolites are thought to initiate colorectal cancer via DNA crosslinking. Here we report confirmation of the structural assignment of the complex clb product precolibactin 886 via a biomimetic synthetic pathway. We show that an α-ketoimine linear precursor undergoes spontaneous cyclization to precolibactin 886 on HPLC purification Studies of this α-ketoimine and the related α-dicarbonyl revealed that these compounds are unexpectedly susceptible to nucleophilic cleavage under mildly basic conditions. This cleavage pathway forms other known clb metabolites or biosynthetic intermediates and explains the difficulties in isolating fully mature biosynthetic products. This cleavage also accounts for a recently identified colibactin-adenine adduct. The colibactin peptidase ClbP deacylates synthetic precolibactin 886 to form a non-genotoxic pyridone, which suggests precolibactin 886 lies off the path of the major biosynthetic route.

Nature Chemistry published new progress about Biomimetic synthesis. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, COA of Formula: C12H18N2O4S.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Bernier, Jean Luc; Houssin, Raymond; Henichart, Jean Pierre published the artcile< Analog of dolastatin 3. Synthesis, proton NMR studies, and spatial conformation>, COA of Formula: C12H18N2O4S, the main research area is dolastatin 3 analog preparation conformation.

Dolastatin 3 analog I was prepared by deblocking Boc-Pro-Leu-Val-(gly)Thz-(gly)Thz-ONSu (II; Boc = Me3CO2C, NSu = succinimido) by HBr/HOAc and cyclizing the resulting H-Pro-Leu-Val-(gly)Thz-(gly)Thz-ONSu.HBr in pyridine. Boc-Gly-NH2 underwent thionation via the Lawesson procedure to give Boc-Gly(S)-NH2, which was cyclized with CH3COCO2Et to give Boc-(gly)Thz-OEt (III). III was Boc-deblocked by HBr/HOAc to give H-(gly)Thz-OEt.HBr (IV), whereas III was saponified to give Boc-(gly)Thz-OH (V). V was coupled with IV by DCC/HOBt to give Boc-(gly)Thz-(gly)Thz-OEt, which was Boc-deblocked and then coupled with Boc-Pro-Leu-Val-OH by DCC/HOBt to give Boc-Pro-Leu-Val-(gly)Thz-(gly)Thz-OEt, which was converted into II. A spatial mol. conformation of I was proposed based on 1H NMR spectroscopy.

Tetrahedron published new progress about Cyclic peptides Role: SPN (Synthetic Preparation), PREP (Preparation). 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, COA of Formula: C12H18N2O4S.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica