Day: October 20, 2022

Tao, Zhi-Fu; Chen, Zehan; Bui, Mai-Ha; Kovar, Peter; Johnson, Eric; Bouska, Jennifer; Zhang, Haiying; Rosenberg, Saul; Sowin, Thomas; Lin, Nan-Horng published the artcile< Macrocyclic ureas as potent and selective Chk1 inhibitors: An improved synthesis, kinome profiling, structure-activity relationships, and preliminary pharmacokinetics>, Formula: C4H3NOS, the main research area is macrocyclic urea preparation selective Chk1 inhibitor; structure macrocyclic urea selectivity Chk1 inhibitor pharmacokinetics; doxorubicin macrocyclic urea combination antitumor activity; kinase selectivity inhibition macrocyclic urea; amine protection key step preparation macrocyclic urea; trimethylsilylethoxycarbonyl group protection amine key step preparation macrocyclic urea.

Macrocyclic ureas such as I [R = H, H2N, MeNH, Me2N, (HOCH2CH2)2N, HOCH2CH2NH, 5-thiazolylmethylamino, 4-pyridinecarbonylamino, 2-chloro-4-pyridinecarbonylamino, (S)-MeCH(NH2)CONH, 2-(4-morpholinyl)ethoxycarbonylamino, 2-oxo-3-oxazolidinyl, HO, HOCH2CH2O, HO(CH2)3O, MeO(CH2)3, 2-(4-morpholinyl)ethoxy, 3-(4-morpholinyl)propoxy, 4-(1-piperidinyl)-1-piperidinecarbonyloxy, (HO)2P(:O); X = CH2CH2, CH:CH] are prepared as selective Chk1 kinase inhibitors and as agents for the sensitization of tumor cells to doxorubicin for potential use as anticancer agents. The structure-activity relationship for Chk1 inhibition of substituted 14-membered urea macrocycles is determined, leading to the identification of sixteen compounds which are effective inhibitors of Chk1. The active urea macrocycles significantly sensitize tumor cells to the DNA-damaging antitumor agent doxorubicin in a cell-based assay and efficiently abrogate the doxorubicin-induced G2/M and camptothecin-induced S checkpoints. The inhibition of a panel of 120 kinases by I (R = 5-thiazolemethylamino; X = CH2CH2; II) is determined; II inhibits Chk1 at 100-fold lower concentrations than any of the other kinases in the panel. Pharmacokinetic studies of I (R = H; X = CH2CH2, CH2CH2CH2) suggest that 14-membered macrocycles such as I (R = H; X = CH2CH2) may possess better pharmacokinetic properties than their 15-membered counterparts such as I (R = H; X = CH2CH2CH2). An improved method for the preparation of amine-containing urea macrocycles I [R = H2N; X = CH:CH, CH2CH2] is determined; protection of the free amino group of a bisallyl diaryl urea intermediate with the trimethylsilylethoxycarbonyl group allows ring-closing macrocyclocondensation in the presence of the Hoveyda-Grubbs catalyst without the formation of inseparable and highly colored byproducts.

Bioorganic & Medicinal Chemistry Letters published new progress about Antitumor agents. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Formula: C4H3NOS.

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

Durant, Graham J.; Ganellin, C. Robin; Parsons, Michael E. published the artcile< Chemical differentiation of histamine H1- and H2-receptor agonists>, Category: thiazole, the main research area is histamine analog receptor agonist.

Histamine [51-45-6] H1- and H2-receptor agonist activities of 10 histamine derivatives and analogs were determined and related to chem. structure and tautomeric form. Nontautomeric 2-(2-aminoethyl)thiazole-2HCl (I-2HCl) [56933-57-4] and 2-(2-aminoethyl)pyridine-2HCl (II-2HCl) [3343-39-3] are highly selective H1-receptor agonists (H1:H2 ∼90:1 and 30:1, resp.), while 4-methylhistamine-2HCl [36376-47-3] is a selective H2-receptor agonist.

Journal of Medicinal Chemistry published new progress about Receptors Role: BIOL (Biological Study). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Category: thiazole.

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

Pan, Liangkun; Zheng, Qiang; Chen, Yu; Yang, Rui; Yang, Yanyan; Li, Zhongjun; Meng, Xiangbao published the artcile< Design, synthesis and biological evaluation of novel naphthoquinone derivatives as IDO1 inhibitors>, Recommanded Product: Thiazole-5-carboxyaldehyde, the main research area is naphthoquinone derivative preparation indoleamine dioxygenase inhibitor anticancer activity SAR; Cancer immunotherapy; Indoleamine 2,3-dioxygenase 1; Naphthoquinone derivatives; Tryptophan 2,3-dioxygenase.

Indoleamine 2,3-dioxygenase 1 mediated kynurenine pathway of tryptophan degradation is identified as an appealing and novel target in immunotherapy for the treatment of cancer. In this study, a novel series of naphthoquinone derivatives were synthesized, characterized and evaluated for their inhibitory activities against IDO1, and their structure-activity relationship was investigated. Among them, five compounds, e.g., I,displayed potent IDO1 inhibitory activities with IC50 values ranging between 18 and 61 nM, which are more potent than INCB024360 undergoing clin. trial III evaluation. In addition, three compounds, e.g. II, decreased the kynurenine levels in rat plasma by 30%-50%. Compounds exhibiting excellent IDO1 inhibitory activities were also evaluated for their inhibitory activities against tryptophan 2,3-dioxygenase (TDO). Of which, compound II (IDO1 IC50 = 120 nM) showed promising TDO inhibition (IC50 72 nM) and was identified as an IDO1/TDO dual inhibitor.

European Journal of Medicinal Chemistry published new progress about Antitumor agents. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Recommanded Product: Thiazole-5-carboxyaldehyde.

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

Chadha, Ridhima; Das, Abhishek; Kapoor, Sudhir; Maiti, Nandita published the artcile< Surface-induced dimerization of 2-thiazoline-2-thiol on silver and gold nanoparticles: A surface enhanced Raman scattering (SERS) and density functional theoretical (DFT) study>, SDS of cas: 96-53-7, the main research area is surface induced dimerization silver gold nanoparticles enhanced Raman scattering.

The adsorption behavior of an anti-thyroid agent, 2-thiazoline-2-thiol (TT) on silver (Ag) and gold (Au) nanoparticles (NPs) was studied using surface enhanced Raman scattering (SERS) and d. functional theory (DFT). The tautomers of TT involved in the surface adsorption processes were identified. Raman scattering studies indicated the predominance of the thione form in solid and the thiol tautomer in aqueous solution SERS studies of TT functionalized Ag (TT-Ag) and Au NPs (TT-Au) showed maximum enhancement for 1μM concentration, suggesting monolayer coverage. Surface induced dimerization of TT was evident from SERS and DFT. The appearance of prominent peaks at 484 (S-S stretch) and 317 (CSS bend) cm-1 for TT-Ag revealed the formation of disulfide dimer, while the emergence of a distinct band at 2124 cm-1 (H-bonded S-H stretch) for TT-Au indicated the development of H-bonded dimer. Thus, in the present study, selective formation of disulfide dimer and the H-bonded dimer was observed on the surface of Ag and Au NPs, resp. In Inaddn., the thiol tautomer was found to be exclusively bound to the metal surface, via the thiazoline ring N atom. In this work, a qual. relation between the strength of TT-metal charge transfer complex and inter-mol. association of TT on the surface of metal NPs was established. This study, thus paves the way for designing novel metal nanosubstrates that can be exploited for studying interesting surface phenomenon, viz. surface induced dimerization or rearrangement reactions, surface catalysis, etc. as well as for designing valuable drugs suitable for chelation therapy.

Journal of Molecular Liquids published new progress about Adsorption. 96-53-7 belongs to class thiazole, and the molecular formula is C3H5NS2, SDS of cas: 96-53-7.

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

Zhang, Min; Fan, Shiyong; Zhou, Xinbo; Xie, Fei; Li, Song; Zhong, Wu published the artcile< Design, synthesis and biological evaluation of 2-hydrazinyladenosine derivatives as A2A adenosine receptor ligands>, Recommanded Product: Thiazole-5-carboxyaldehyde, the main research area is hydrazinyladenosine human adenosine receptor G protein; mol docking adenosine receptor ligand hydrazinyladenosine synthesis nucleoside; A(2A) agonist; Fragment-based drug design; G protein-coupled receptors.

To obtain potential A2A adenosine receptor agonists, a series of 2-hydrazinyladenosine derivatives were synthesized and assayed for adenosine receptors activity using radioligand binding activity assays. The binding activity of the subtypes was examined, and the structure-activity relationship of this class of compounds at the A2A receptor was investigated. A fragment-based computer-aided design method was used to modify the 2-position side chain structures with different structural fragments, and the newly generated mols. were docked to the A2A receptor to assess scoring and screening activity. To synthesize compounds with better scoring activity, the newly synthesized compounds were tested for in vitro receptor binding activity. 2-Hydrazinyladenosine derivatives of 32 new structural types were designed and synthesized, with the most potent adenosine derivative I exhibiting a Ki value of 1.8 nM for A2AAR and significant selectivity for the A2A receptor compared to the A1 receptor. In addition to, other compounds also exhibited potent A2A receptor selectivity, with Ki values for the A2A receptor of 6.4, 20, 67 and 6.3 nM, resp. We also found that compound II has a high A1 receptor selectivity, with a Ki value for the A1 receptor of 4.5 nM. Further functional assays also demonstrated that these compounds have potent A2A receptor agonist activity. The study shows the applicability of an in silico fragment-based mol. design for rational lead optimization in A2AAR.

European Journal of Medicinal Chemistry published new progress about Adenosine A1 receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Recommanded Product: Thiazole-5-carboxyaldehyde.

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

Wang, Xinmou; Chen, Yuming; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin published the artcile< Construction of 2-(2-Arylphenyl)azoles via Cobalt-Catalyzed C-H/C-H Cross-Coupling Reactions and Evaluation of Their Antifungal Activity>, COA of Formula: C7H9NO2S, the main research area is biaryl azole cobalt catalyst agrochem fungicide; azole biphenyl amide cross coupling reaction.

Although compounds with a 2-(2-arylphenyl) benzoxazole motif are biol. important, there are only a few methods for synthesizing them. Herein, authors report an efficient method for synthesis of such compounds by means of cobalt-catalyzed C-H/C-H cross-coupling reactions. This method has a broad substrate scope and good tolerance for sensitive functional groups. In addition, authors demonstrate that introducing a heteroarene moiety to biphenyl compounds enhanced their antifungal activity.

Organic Letters published new progress about Agrochemical fungicides. 20582-55-2 belongs to class thiazole, and the molecular formula is C7H9NO2S, COA of Formula: C7H9NO2S.

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

Kitada, Nobuo; Saito, Ryohei; Obata, Rika; Iwano, Satoshi; Karube, Kazuma; Miyawaki, Atsushi; Hirano, Takashi; Maki, Shojiro A. published the artcile< Development of near-infrared firefly luciferin analogue reacted with wild-type and mutant luciferases>, COA of Formula: C11H8N2O3S2, the main research area is firefly luciferin luciferase near IR spectroscopy chemiluminescence; Akaluc; Photinus pyralis luciferase; TokeOni; luciferin analogues; luciferin-luciferase reaction; mutant luciferase; near-infrared bioluminescence.

Interestingly, only the D-form of firefly luciferin produces light by luciferin-luciferase (L-L) reaction. Certain firefly luciferin analogs with modified structures maintain bioluminescence (BL) activity; however, all L-form luciferin analogs show no BL activity. To this date, our group has developed luciferin analogs with moderate BL activity that produce light of various wavelengths. For in vivo bioluminescence imaging, one of the important factors for detection sensitivity is tissue permeability of the number of photons emitted by L-L reaction, and the wavelengths of light in the near-IR (NIR) range (700-900 nm) are most appropriate for the purpose. Some NIR luciferin analogs by us had performance for in vivo experiments to make it possible to detect photons from deep target tissues in mice with high sensitivity, whereas only a few of them can produce NIR light by the L-L reactions with wild-type luciferase and/or mutant luciferase. Based on the structure-activity relationships, we designed and synthesized here a luciferin analog with the 5-allyl-6-dimethylamino-2-naphthylethenyl moiety. This analog exhibited NIR BL emissions with wild-type luciferase (max = 705 nm) and mutant luciferase AlaLuc (max = 655 nm).

Chirality published new progress about Bioluminescence. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, COA of Formula: C11H8N2O3S2.

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

Kozikowski, Alan P.; Chen, Yufeng; Gaysin, Arsen; Chen, Bin; D’Annibale, Melissa A.; Suto, Carla M.; Langley, Brett C. published the artcile< Functional Differences in Epigenetic Modulators-Superiority of Mercaptoacetamide-Based Histone Deacetylase Inhibitors Relative to Hydroxamates in Cortical Neuron Neuroprotection Studies>, SDS of cas: 57493-24-0, the main research area is mercaptoacetamide derivative preparation structure histone deacetylase inhibitor neuroprotectant neuron.

The authors compare the ability of two structurally different classes of epigenetic modulators, namely, histone deacetylase (HDAC) inhibitors containing either a hydroxamate or a mercaptoacetamide as the zinc binding group, to protect cortical neurons in culture from oxidative stress-induced death. This study reveals that some of the mercaptoacetamide-based HDAC inhibitors are fully protective, whereas the hydroxamates show toxicity at higher concentrations The present results appear to be consistent with the possibility that the mercaptoacetamide-based HDAC inhibitors interact with a different subset of the HDAC isoenzymes [less activity at HDAC1 and 2 correlates with less inhibitor toxicity], or alternatively, are interacting selectively with only the cytoplasmic HDACs that are crucial for protection from oxidative stress.

Journal of Medicinal Chemistry published new progress about Neuron. 57493-24-0 belongs to class thiazole, and the molecular formula is C9H7N3O2S, SDS of cas: 57493-24-0.

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

Bittel, Amy M.; Davis, Ashley M.; Wang, Lei; Nederlof, Michel A.; Escobedo, Jorge O.; Strongin, Robert M.; Gibbs, Summer L. published the artcile< Varied Length Stokes Shift BODIPY-Based Fluorophores for Multicolor Microscopy>, Safety of 4-(Thiazol-2-yl)benzaldehyde, the main research area is boron dipyrromethene aromatic aldehyde fluorophore stokes shift multicolor microscopy.

Multicolor microscopy tools necessary to localize and visualize the complexity of subcellular systems are limited by current fluorophore technol. While com. fluorophores cover spectral space from the UV to the near IR region and are optimized for conventional bandpass based fluorescence microscopy, they are not ideal for highly multiplexed fluorescence microscopy as they tend to have short Stokes shifts, restricting the number of fluorophores that can be detected in a single sample to four to five. Herein, we synthesized a library of 95 novel boron-dipyrromethene (BODIPY)-based fluorophores and screened their photophys., optical and spectral properties for their utility in multicolor microscopy. A subset of our BODIPY-based fluorophores yielded varied length Stokes shifts probes, which were used to create a five-color image using a single excitation with confocal laser scanning microscopy for the first time. Combining these novel fluorophores with conventional fluorophores could facilitate imaging in up to nine to ten colors using linear unmixing based microscopy approaches.

Scientific Reports published new progress about Biological imaging. 198904-53-9 belongs to class thiazole, and the molecular formula is C10H7NOS, Safety of 4-(Thiazol-2-yl)benzaldehyde.

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