Day: October 18, 2022

Surendra Kumar, Radhakrishnan; Moydeen, Meera; Al-Deyab, Salem S.; Manilal, Aseer; Idhayadhulla, Akbar published the artcile< Synthesis of new morpholine-connected pyrazolidine derivatives and their antimicrobial, antioxidant, and cytotoxic activities>, SDS of cas: 1003-32-3, the main research area is morpholine pyrazolidine derivative synthesis antimicrobial antioxidant anticancer; Antimicrobial activity; Antioxidant activity; Cytotoxic activity; Morpholine-connected pyrazolidine; Pyrrolidine metal-free catalysis.

A simple and convenient one-pot four-component synthesis of morpholine-connected pyrazolidine derivatives 2a-f and 4a-f was developed using direct metal-free catalysis, with the identities of the synthesized compounds confirmed by IR, NMR (1H and 13C), mass spectrometry, and elemental anal. The prepared compounds were inspected for antimicrobial, antioxidant, and cytotoxic activities. Antimicrobial and antifungal activities against five bacterial and four fungal pathogens, resp., were investigated using the disk diffusion technique. In antibacterial activity, compounds 2d and 2f (I and II, resp., MIC = 2 μg/mL) exhibited significantly higher activity than the standard ciprofloxacin. The results of antifungal assay showed that the activity of compound 4a (IV, MIC = 0.5 μg/mL) was significantly higher than the standard clotrimazole. Antioxidant activity was screened based on ABTS·+ radical scavenging and linoleic acid peroxidation performance. Compound 4a showed substantial antioxidant (91.3%) activities, as compared with the Trolox standard Cytotoxicity was evaluated using HepG2 (liver), HeLa (cervical), and MCF-7 (breast) cancer cell lines, with high toxicities observed for 2b (III, GI50 = 12.2 μm) and 4a (GI50 = 07.8 μm).

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

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

Flipo, Marion; Desroses, Matthieu; Lecat-Guillet, Nathalie; Villemagne, Baptiste; Blondiaux, Nicolas; Leroux, Florence; Piveteau, Catherine; Mathys, Vanessa; Flament, Marie-Pierre; Siepmann, Juergen; Villeret, Vincent; Wohlkonig, Alexandre; Wintjens, Rene; Soror, Sameh H.; Christophe, Thierry; Jeon, Hee Kyoung; Locht, Camille; Brodin, Priscille; Deprez, Benoit; Baulard, Alain R.; Willand, Nicolas published the artcile< Ethionamide Boosters. 2. Combining Bioisosteric Replacement and Structure-Based Drug Design To Solve Pharmacokinetic Issues in a Series of Potent 1,2,4-Oxadiazole EthR Inhibitors>, Electric Literature of 1003-32-3, the main research area is oxadiazole EthR inhibitor preparation structure tuberculosis pharmacokinetics.

Mycobacterial transcriptional repressor EthR controls the expression of EthA, the bacterial monooxygenase activating ethionamide, and is thus largely responsible for the low sensitivity of the human pathogen Mycobacterium tuberculosis to this antibiotic. We recently reported structure-activity relationships of a series of 1,2,4-oxadiazole EthR inhibitors leading to the discovery of potent ethionamide boosters. Despite high metabolic stability, pharmacokinetic evaluation revealed poor mice exposure; therefore, a second phase of optimization was required. Herein a structure-property relationship study is reported according to the replacement of the two aromatic heterocycles: 2-thienyl and 1,2,4-oxadiazolyl moieties. This work was done using a combination of structure-based drug design and in vitro/ex vivo evaluations of ethionamide boosters on the targeted protein EthR and on the human pathogen Mycobacterium tuberculosis. Thanks to this process, we identified compound 42 (BDM41906), which displays improved efficacy in addition to high exposure to mice after oral administration.

Journal of Medicinal Chemistry published new progress about Homo sapiens. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Electric Literature of 1003-32-3.

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

Watanabe, Hiroaki; Yamaori, Satoshi; Kamijo, Shinobu; Aikawa, Kaori; Ohmori, Shigeru published the artcile< In vitro inhibitory effects of sesamin on CYP4F2 activity>, Formula: C11H8N2O3S2, the main research area is microsome CYP4F2 enzyme inhibition sesamin NADPH; CYP4F2; inactivation; inhibition; sesamin.

Sesamin is a major lignan in sesame seeds, and a recent meta-anal. of controlled trials indicated that sesamin intake decreases blood pressure. The antihypertensive effect of sesamin has been suggested to be due to sesamin-mediated suppression of 20-hydroxyeicosatetraenoic acid production catalyzed by CYP4F2. However, the detailed mechanism underlying inhibition of CYP4F2 function by sesamin remains unclear. In this study, the effects of sesamin on catalytic activity of CYP4F2 were investigated in vitro. Sesamin inhibited luciferin-4F2/3 O-dealkylase activity of recombinant human CYP4F2 with an IC50 value of 0.381μM. When preincubated in the presence of reduced NADP (NADPH) for 20 min, sesamin potentiated the inhibition of CYP4F2 activity. Moreover, kinetic anal. of the inactivation revealed that sesamin showed a preincubation time- and concentration-dependent inhibition of CYP4F2 activity yielding a maximal inactivation rate constant (kinact) value of 0.354 min-1 and half-maximal inhibitory concentration (KI) value of 1.12μM. The inactivation of CYP4F2 by sesamin required NADPH. These results indicated that sesamin is a mechanism-based inactivator of human CYP4F2.

Biological & Pharmaceutical Bulletin published new progress about Enzyme inhibition kinetics. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Formula: C11H8N2O3S2.

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

Feng, Daijun; Barton, George; Scott, Colleen N. published the artcile< Synthesis of 2,5-Dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione: A Diketopyrrolopyrrole Scaffold for the Formation of Alkenyldiketopyrrolopyrrole Compounds>, COA of Formula: C4H3NOS, the main research area is dibutyldimethylpyrrolopyrrole dione preparation diketopyrrolopyrrole scaffold; divinyl substituted diketopyrrolopyrrole carbon hydrogen functionalization.

This manuscript describes an unprecedented and efficient synthesis of a new DPP scaffold, 2,5-dibutyl-3,6-dimethyl-1H,2H,4H,5H-pyrrolo[3,4-c]pyrrole-1,4-dione (DMDPP), containing Me groups at the 3,6-positions as a precursor to preparing 3,6-divinyl-substituted DPP compounds Subsequently, following the synthesis of DMDPP, we performed an efficient and mild C-H functionalization of the Me groups with a variety of aromatic aldehydes to synthesize the first examples of 3,6-divinyl-substituted DPP compounds in moderate to good yields.

Organic Letters published new progress about Aldol condensation. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, COA of Formula: C4H3NOS.

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

Kotlyar, V. M.; Kolomoitsev, O. O.; Tarasenko, D. O.; Bondarenko, Y. H.; Butenko, S. V.; Buravov, O. V.; Kotlyar, M. I.; Roshal, A. D. published the artcile< Prospective biologically active compounds based on 5-formylthiazole>, Name: Thiazole-5-carboxyaldehyde, the main research area is thiazole pyrimidine benzimidazole chalcone preparation.

Thiazole cycle is a structural element of many compounds which have potential or already proven fungicidal, bactericidal and antiviral activity. A number of compounds and materials with promising antimicrobial effects can be functionalized by introducing the thiazole component into their composition Among them, there are photoreactive materials, complexing agents, convenient building blocks for the synthesis of biol. active compounds etc. A number of synthetic approaches, as well as optimized conditions for obtaining new thiazole-containing compounds, which have the prospect of practical application based on their physicochem. properties and potential biol. activity has been developed.

Functional Materials published new progress about Amidines Role: RCT (Reactant), RACT (Reactant or Reagent). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Name: Thiazole-5-carboxyaldehyde.

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

Azzarelli, Nicholas; Ponnala, Shashikanth; Aguirre, Alexander; Dampf, Sara J.; Davis, Margaret P.; Ruggiero, Michael T.; Lopez Diaz, Valerie; Babich, John W.; Coogan, Michael; Korter, Timothy; Doyle, Robert P.; Zubieta, Jon published the artcile< Defining the origins of multiple emission/excitation in rhenium-bisthiazole complexes>, Name: Thiazole-5-carboxyaldehyde, the main research area is rhenium bisthiazole complex preparation fluorescence emission excitation mechanism photophys; crystal structure mol rhenium bisthiazole complex optimized DFT.

The underlying mechanism of the unusual emissive behavior of [Re(CO)3-1,1-bis-4-thiazole-(1,4)-diaminobutane] bromide (4-BT) has been investigated. Synthesis and spectroscopic characterization of structurally similar isomers [Re(CO)3-1,1-bis-2-thiazole-(1,4)-diaminobutane] bromide (2-BT) and the location of triplet states, solid state and low temperature spectroscopic measurements, and DFT calculations show that the photophys. properties are not due to photoisomerization as previously hypothesized. The results show that the unusual emissive behavior is not observed in structural isomers, is specific to the previously reported complex, 4-BT, and may arise from vibrational energy relaxation and vibrational cooling. Translation of the unusual emissive behavior to the solid state offers an interesting platform allowing this complex to be potentially utilized as a probe, sensor or photonic device.

Inorganica Chimica Acta published new progress about Charge transfer transition. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Name: Thiazole-5-carboxyaldehyde.

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

Dondoni, Alessandro; Fantin, Giancarlo; Fogagnolo, Marco; Medici, Alessandro; Pedrini, Paola published the artcile< Synthesis of (trimethylsilyl)thiazoles and reactions with carbonyl compounds. Selectivity aspects and synthetic utility>, Computed Properties of 1003-32-3, the main research area is silylthiazole; thiazole; synthon silylthiazole; carbonyl compound silylthiazole reaction.

Synthetic routes to all possible regioisomeric mono- and bis(trimethylsilyl)thiazoles as well as to the tris(trimethylsilyl) derivative via lithiation-silylation sequences of the thiazole ring followed by selective protodesilylation in some cases are described. (Trimethylsilyl)thiazoles serve as thiazolyl donor synthons upon reaction with carbonyl compounds (ketenes, acyl chlorides, aldehydes) for the preparation of mono- and bis-substituted thiazoles in very good yields. Carbodesilylation occurs more readily at the 2- than the 5-position, whereas no reaction takes place at the 4-position. A mechanism via a thiazolium 2-ylide as an intermediate is suggested for the carbodesilylation at the 2-position.

Journal of Organic Chemistry published new progress about Carbonyl compounds (organic) Role: RCT (Reactant), RACT (Reactant or Reagent). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Computed Properties of 1003-32-3.

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

Hettie, Kenneth S.; Teraphongphom, Nutte Tarn; Ertsey, Robert D.; Rosenthal, Eben L.; Chin, Frederick T. published the artcile< Targeting intracranial patient-derived glioblastoma (GBM) with a NIR-I fluorescent immunoconjugate for facilitating its image-guided resection>, Computed Properties of 2591-17-5, the main research area is glioblastoma human fluorescent immunoconjugate.

Glioblastoma multiforme (GBM) is the most aggressive form of primary brain tumor type and is associated with a high mortality rate borne out of such affording a survival rate of only 15 mo. GBM aggressiveness is associated with the overexpression of epidermal growth factor receptor (EGFR) and its mutants. Targeting GBM with therapeutics is challenging because the blood-brain barrier (BBB) permits primarily select small-mol. entities across its semipermeable blockade. However, recent preclin. data suggest that large biomols., such as the anti-EGFR antibody therapeutic, cetuximab, could be capable of bypassing the BBB despite the relative enormity of its size. As such, we set forth to establish the feasibility of utilizing an EGFR-targeting near-IR-I (NIR-I) fluorescent construct in the form of an immunoconjugate (cetuxmimab-IRDye800) to achieve visual differentiation between diseased brain tissue arising from a low-passage patient-derived GBM cell line (GBM39) and healthy brain tissue via utilizing orthotopic intracranial murine GBM39 tumor models for in vivo and ex vivo evaluation such that by doing so would establish proof of concept for ultimately facilitating its in vivo fluorescence-guided resection and ex vivo surgical back-table pathol. confirmation in the clinic. As anticipated, we were not capable of distinguishing between malignant tumor tissue and healthy tissue in resected intact and slices of whole brain ex vivo under white-light illumination (WLI) due to both the diseased tissue and healthy tissue appearing virtually identical to the unaided eye. However, we readily observed over an average 6-fold enhancement in the fluorescence emission in the resected intact whole brain ex vivo when performing NIR-I fluorescence imaging (FLI) on the cohort of GBM39 tumor models that were administered the immunoconjugate compared to controls. In all, we laid the initial groundwork for establishing that NIR-I fluorescent immunoconjugates (theranostics) such as cetuximab-IRDye800 can bypass the BBB to visually afford GBM39 tumor tissue differentiation for its image-guided surgical removal.

RSC Advances published new progress about Biochemical compounds Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Computed Properties of 2591-17-5.

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

Zheng, Shilong; Zhong, Qiu; Xi, Yulan; Mottamal, Madhusoodanan; Zhang, Qiang; Schroeder, Richard L.; Sridhar, Jayalakshmi; He, Ling; McFerrin, Harris; Wang, Guangdi published the artcile< Modification and Biological Evaluation of Thiazole Derivatives as Novel Inhibitors of Metastatic Cancer Cell Migration and Invasion>, Related Products of 324579-90-0, the main research area is thiazole derivative preparation antitumor cancer metastasis.

Fascin has recently emerged as a potential therapeutic target, as its expression in cancer cells is closely associated with tumor progression and metastasis. Following the initial discovery of a series of thiazole derivatives that demonstrated potent antimigration and antiinvasion activities via possible inhibition of fascin function, we report here the design and synthesis of 63 new thiazole derivatives by further structural modifications in search of more potent fascin inhibitors. The 5 series of analogs with longer alkyl chain substitutions on the thiazole nitrogen exhibited greater antimigration activities than those with other structural motifs. The most potent analog, 5p, inhibited 50% of cell migration at 24 nM. Moreover, the thiazole analogs showed strong antiangiogenesis activity, blocking new blood vessel formation in a chicken embryo membrane assay. Finally, a functional study was conducted to investigate the mechanism of action via interaction with the F-actin bundling protein fascin.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 324579-90-0 belongs to class thiazole, and the molecular formula is C6H8N2S, Related Products of 324579-90-0.

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

Kagiya, Go; Sato, Ayaka; Ogawa, Ryohei; Hatashita, Masanori; Kato, Mana; Kubo, Makoto; Kojima, Fumiaki; Kawakami, Fumitaka; Nishimura, Yukari; Abe, Naoya; Hyodo, Fuminori published the artcile< Real-time visualization of intratumoral necrosis using split-luciferase reconstitution by protein trans-splicing>, Quality Control of 2591-17-5, the main research area is intratumoral necrosis luciferase protein splicing; bioluminescent imaging; cell death; extein; intein; necrosis; necrosis imaging reporter; protein trans-splicing; split-luciferase reconstitution.

Necrosis, a form of cell death, occurs not only with the development of various diseases but also with a tumor tissue response to cancer treatment. Therefore, pursuing progress for cancer therapy through induction of necrosis may be one of the most effective approaches for cancer eradication. We herein describe the development of a real-time imaging system to visualize intratumoral necrosis. The system is composed of two types of cells expressing either one of two necrosis imaging reporters that consist of a DnaE intein sequence linking to one of two split-luciferase fragments. When necrosis occurs in a tumor composed of both of the cells, the two types of leaked reporters can reconstitute the enzymic activity as a result of protein trans-splicing and thereby emit bioluminescence in the presence of the substrate. This system, which was constructed with shrimp-derived luciferase, allowed in vitro imaging of necrosis. We further confirmed real-time imaging of intratumoral necrosis caused by phys. or chem. tissue disruption, validating its application in in vivo necrosis imaging. Thus, the constructed imaging system could be a powerful tool for the optimization of the therapeutic condition for cancer therapy and for the evaluation of novel anticancer drugs targeting necrosis.

Molecular Therapy–Oncolytics published new progress about Antitumor agents. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Quality Control of 2591-17-5.

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