Category: 96929-05-4

Patel, Bhargav A.; Abel, Biebele; Barbuti, Anna Maria; Velagapudi, Uday Kiran; Chen, Zhe-Sheng; Ambudkar, Suresh V.; Talele, Tanaji T. published the artcile< Comprehensive Synthesis of Amino Acid-Derived Thiazole Peptidomimetic Analogues to Understand the Enigmatic Drug/Substrate-Binding Site of P-Glycoprotein>, Safety of Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is thiazole peptidomimetic synthesis ATPase stimulator inhibitor structure activity; drug substrate binding P glycoprotein antitumor agent mol docking; peptide coupling Boc protection.

A novel set of 64 analogs based on our lead compound (I) was designed and synthesized with an initial objective of understanding the structural requirements of ligands binding to a highly perplexing substrate-binding site of P-gp and their effect on modulating the ATPase function of the efflux pump. Compound I, a stimulator of P-gp ATPase activity, was transformed to ATPase inhibitory compounds (II), (III) and (IV). The ATPase inhibition by these compounds was predominantly contributed by the presence of a cyclohexyl group in lieu of the 2-aminobenzophenone moiety of I. The 4,4-difluorocyclohexyl analogs III and IV inhibited the photolabeling by [125I]-IAAP, with IC50 values of 0.1 and 0.76 M, resp. Selected compounds were shown to reverse paclitaxel resistance in HEK293 cells overexpressing P-gp and were selective toward P-gp over CYP3A4. Induced-fit docking highlighted a plausible binding pattern of inhibitory compounds in the putative-binding pocket of P-gp. The current study underscores the stringent requirement by P-gp to bind to chem. similar mols.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 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

Aihara, Kazuhiro; Kano, Yuko; Shiokawa, Sohjiro; Sasaki, Toshiro; Setsu, Fumihito; Sambongi, Yumiko; Ishii, Miyuki; Tohyama, Kazuyo; Ida, Takashi; Tamura, Atsushi; Atsumi, Kunio; Iwamatsu, Katsuyoshi published the artcile< CP0569, A New Broad-Spectrum Injectable Carbapenem. Part 1: Synthesis and Structure-Activity Relationships>, Safety of Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is methylcarbapenem antimicrobial activity.

A series of 1β-methylcarbapenems bearing an (imidazo[5,1-b]thiazolium-6-yl)methyl moiety, a 5,5-fused heterobicycle, at the C-2 position was synthesized and evaluated for in vitro antibacterial activities. CP0569 (1r) and its analogs showed potent antibacterial activities against Gram-pos. bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), and Gram-neg. bacteria, including Pseudomonas aeruginosa. Moreover, CP0569 (1r) exhibited stronger antibacterial activity against MRSA and higher resistance to renal dehydropeptidase-1 (DHP-1) than any currently marketed carbapenems, i.e., imipenem (IPM), panipenem (PAPM), and meropenem (MEPM).

Bioorganic & Medicinal Chemistry published new progress about Antimicrobial agents. 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

Schneider, Tanya L.; Walsh, Christopher T.; O’Connor, Sarah E. published the artcile< Utilization of Alternate Substrates by the First Three Modules of the Epothilone Synthetase Assembly Line>, Product Details of C12H18N2O4S, the main research area is substrate specificity epothilone synthetase Sorangium serine polyketide oxazole analog.

The epothilones, a family of macrolactone natural products produced by the myxobacterial species Sorangium cellulosum, are of current clin. interest as antitumor agents. Inspection of the structure of the epothilones suggests a hybrid polyketide/nonribosomal peptide biosynthetic origin, and the recent sequencing of the epothilone biosynthetic gene cluster has validated this proposal. Here we have examined unnatural substrates with the first two enzymes of the biosynthetic pathway, EpoA and EpoB, to investigate the enzymic construction of alternate heterocyclic structures and the subsequent elongation of these products by the third enzyme of the pathway, EpoC. The epothilone biosynthetic machinery can utilize serine to install an oxazole in place of a thiazole in the epothilone structure and will tolerate functionalized donor groups from the EpoA-ACP domain to produce epothilone fragments modified at the C21 position. These studies with the early enzymes of the epothilone biosynthesis cluster suggest that combinatorial biosynthesis may be a viable means for producing a variety of epothilone analogs that incorporate diversity into the heterocycle starter unit.

Journal of the American Chemical Society published new progress about Sorangium cellulosum. 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

Wahyudi, Hendra; Tantisantisom, Worawan; Liu, Xuechao; Ramsey, Deborah M.; Singh, Erinprit K.; McAlpine, Shelli R. published the artcile< Synthesis, structure-activity analysis, and biological evaluation of sanguinamide B analogues>, Quality Control of 96929-05-4, the main research area is sanguinamide B analog synthesis antibacterial structure activity twitching motility; natural product antibiotic sanguinamide conformation conformer; peptide coupling Hantzsch cyclocondensation macrocyclization.

We report the first synthesis of sanguinamide B analogs. Substituting N-methylated (N-Me) amino acids, glycine (Gly), and L- or D-phenylalanine (Phe) into the backbone of sanguinamide B showed that only L- and D-Phe residues controlled the macrocycle conformation. The N-methylated and glycine analogs all had multiple conformations, whereas the L- and D-Phe derivatives only had a single conformation. Testing of all conformer analogs showed that inclusion of an L- or D-Phe was a superior design element than incorporating the N-Me moiety that is often utilized to control macrocyclic conformation. Finally, we show that there is an ideal Phe residue (in this case L-Phe) for generating compounds that have the greatest inhibitory effect on bacterial motility. Our data support the hypothesis that the macrocyclic conformation is dictated by the benzyl moiety requiring a ‘pseudoequatorial’ position, and all other energy considerations are secondary.

Journal of Organic Chemistry published new progress about Antibacterial agents. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Quality Control of 96929-05-4.

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

Sun, Shuang; Oliveira, Bruno L.; Jimenez-Oses, Gonzalo; Bernardes, Goncalo J. L. published the artcile< Radical-Mediated Thiol-Ene Strategy: Photoactivation of Thiol-Containing Drugs in Cancer Cells>, Name: Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is photoactivation thiol containing drug cancer; cage compounds; cancer; photochemistry; radicals; thiol-ene.

Photoactivated drugs provide an opportunity to improve efficacy alongside reducing side-effects in the treatment of severe diseases such as cancer. Described herein is a photoactivation decaging method of isobutylene-caged thiols through a UV-initiated thiol-ene reaction. The method was demonstrated with an isobutylene-caged cysteine, cyclic disulfide-peptide, and thiol-containing drug, all of which were rapidly and efficiently released under mild UV irradiation in the presence of thiol sources and a photoinitiator. Importantly, it is shown that the activity of histone deacetylase inhibitor largazole can be switched off when stapled, but selectively switched on within cancer cells when irradiated with non-phototoxic light.

Angewandte Chemie, International Edition published new progress about Antitumor agents. 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

Xiao, Qiong; Wang, Li-Ping; Jiao, Xiao-Zhen; Liu, Xiao-Yu; Wu, Qian; Xie, Ping published the artcile< Concise total synthesis of largazole>, Recommanded Product: Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is largazole cyclic peptide enantioselective synthesis stereoselective aldol addition; thiazolidinethione chiral auxiliary stereoselective aldol addition largazole enantioselective synthesis; macrolactamization largazole cyclic peptide enantioselective synthesis.

The concise total synthesis of largazole (I) was accomplished. The key step included the use of the Nagao thiazolidinethione auxiliary for a diastereoselective acetate aldol reaction, and it acts as an acylating agent for peptide formation.

Journal of Asian Natural Products Research published new progress about Aldol addition, stereoselective. 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

Billin, Andrew N.; Bantscheff, Marcus; Drewes, Gerard; Ghidelli-Disse, Sonja; Holt, Jason A.; Kramer, Henning F.; McDougal, Alan J.; Smalley, Terry L.; Wells, Carrow W.; Zuercher, William J.; Henke, Brad R. published the artcile< Discovery of Novel Small Molecules that Activate Satellite Cell Proliferation and Enhance Repair of Damaged Muscle>, Formula: C12H18N2O4S, the main research area is muscle regeneration.

Skeletal muscle progenitor stem cells (referred to as satellite cells) represent the primary pool of stem cells in adult skeletal muscle responsible for the generation of new skeletal muscle in response to injury. Satellite cells derived from aged muscle display a significant reduction in regenerative capacity to form functional muscle. This decrease in functional recovery has been attributed to a decrease in proliferative capacity of satellite cells. Hence, agents that enhance the proliferative abilities of satellite cells may hold promise as therapies for a variety of pathol. settings, including repair of injured muscle and age- or disease-associated muscle wasting. Through phenotypic screening of isolated murine satellite cells, we identified a series of 2,4-diaminopyrimidines (e.g., 2) that increased satellite cell proliferation. Importantly, compound 2 was effective in accelerating repair of damaged skeletal muscle in an in vivo mouse model of skeletal muscle injury. While these compounds were originally prepared as c-Jun N-terminal kinase 1 (JNK-1) inhibitors, structure-activity analyses indicated JNK-1 inhibition does not correlate with satellite cell activity. Screening against a broad panel of kinases did not result in identification of an obvious mol. target, so we conducted cell-based proteomics experiments in an attempt to identify the mol. target(s) responsible for the potentiation of the satellite cell proliferation. These data provide the foundation for future efforts to design improved small mols. as potential therapeutics for muscle repair and regeneration.

ACS Chemical Biology published new progress about Heterocyclic aromatic compounds Role: PAC (Pharmacological Activity), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), PREP (Preparation), USES (Uses). 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Formula: C12H18N2O4S.

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

Pena, S.; Fagundez, C.; Medeiros, A.; Comini, M.; Scarone, L.; Sellanes, D.; Manta, E.; Tulla-Puche, J.; Albericio, F.; Stewart, L.; Yardley, V.; Serra, G. published the artcile< Synthesis of cyclohexapeptides as antimalarial and anti-trypanosomal agents>, Related Products of 96929-05-4, the main research area is cyclohexa peptide synthesis antimalarial antitrypanosomal agent structure activity; solid phase peptide synthesis macrocyclization.

Cyclohexapeptide analogs of natural products were obtained in very good yields by a combination of solid-phase peptide synthesis, for the linear peptide, and solution cyclization. The activities against Plasmodium falciparum K1, Trypanosoma brucei brucei and murine macrophages (cell line J774) of these novel compounds and azolic macrocycles, previously reported by us, were evaluated. Seven macrocycles showed submicromolar activities against Plasmodium falciparum K1 and a high selectivity (SI > 125) for the parasite. In addition, two compounds displayed one digit micromolar EC50 against T. brucei brucei and satisfactory selectivity (SI 82 and 95). Preliminary structure-activity relationships are presented.

MedChemComm published new progress about Antimalarials. 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

Fagundez, Catherine; Serra, Gloria published the artcile< Studies on synthesis of amino acid derived thiazoles. Preparation of bis-thiazoles as key fragments of aerucyclamide analogs>, Formula: C12H18N2O4S, the main research area is thiazole bisthiazole preparation.

The scope and limitations of Hantzsch, modified Hantzsch and Kelly methodologies for the synthesis of amino acid derived thiazoles are presented. In addition, the syntheses of bisthiazoles as key fragments of natural products and analogs are described. The Kelly’s methodol. followed by oxidation provides the desired N-Cbz protected thiazole after purification According with the authors’ results the Fmoc or Boc protecting groups are not compatible with the conditions used in this methodol. Modifications of the temperature and reagents used in the Hantzsch thiazole synthesis enabled the preparation of chiral thiazole building blocks without racemization and in good yields.

Heterocyclic Letters published new progress about 96929-05-4. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Formula: C12H18N2O4S.

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

Zhang, Kuojun; Yao, Yiwu; Tu, Zhengchao; Liao, Chenzhong; Wang, Zhen; Qiu, Yatao; Chen, Dong; Hamilton, Dale J.; Li, Zheng; Jiang, Sheng published the artcile< Discovery of class I histone deacetylase inhibitors based on romidpesin with promising selectivity for cancer cells>, Recommanded Product: Ethyl 2-(((tert-butoxycarbonyl)amino)methyl)thiazole-4-carboxylate, the main research area is romidpesin class I histone deacetylase inhibitor cancer cell selectivity; antitumor; class I histone deacetylases; cyclic depsipeptides; inhibitor; structure–activity relationship.

Aim: Class I histone deacetylases (HDACs) are considered to be promising anticancer targets, but selective inhibition of class I HDAC isoforms remains a challenge. Methods & results: Previously, we obtained a selective class I HDAC inhibitor 9 based on a macrocyclic HDAC inhibitor Romidpesin. As our continuous efforts, a library of novel cyclicdepsipeptides based on 9 was established using a convergent synthesis strategy. The most active compounds 10, 16 and 19 selectively inhibit class I HDACs and exhibit promising nanomolar antiproliferative activities against several cancer cell lines with excellent selectivity toward cancer cells over normal cells. Besides, compound 10 demonstrates excellent antitumor effects in human prostate carcinoma PC3 xenograft models with no observed toxicity. Conclusion: These cyclicdepsipeptides show great therapeutic potential as novel anticancer agents for clin. translation.

Future Medicinal Chemistry published new progress about Antitumor agents. 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