Category: 1003-32-3

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

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

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

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

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

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

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

Yin, Liuyan; Wang, Lanzhi published the artcile< Chemo-/regio-selective synthesis of 2-aryl-3-acetyl-2,4-dihydro-1H-5H-1,5-benzodiazepines using Lewis acid, CeCl3·7H2O>, Computed Properties of 1003-32-3, the main research area is dihydrobenzodiazepine aryl acetyl preparation chemoselective regioselective; phenylenediamine aryl aldehyde butynone condensation Lewis acid catalyst.

A unique and efficient method has been developed for the one-pot synthesis of 2-aryl-3-acetyl-2,4-dihydro-1H-5H-1,5-benzodiazepines I (Ar = 2-thiazolyl, 2-thienyl, 4-ClC6H4, etc.) in good yields using o-phenylenediamine, aromatic aldehyde and 3-butyn-2-one in the presence of a catalytic amount of CeCl3·7H2O in ethanol at ambient temperature An exclusive chemo-/regio-selective formation of substituted isomers of 2-aryl-3-acetyl-2,4-dihydro-1H-5H-1,5-benzodiazepines II (Ar = 2-thiazolyl, 2-thienyl, 4-ClC6H4, etc.; R = CH3, F, Cl, Br) was achieved from the different reaction process, by exploiting the strategy based on the variation of electrophilicity of the two electrophilic centers of aromatic aldehyde, 3-butyn-2-one and nucleophilic profiles of substituted o-phenylenediamines. This process offers an easy and efficient synthesis of 2-aryl-3-acetyl-2,4-dihydro-1H-5H-1,5-benzodiazepines in high yields.

Tetrahedron Letters published new progress about Aryl aldehydes 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

Horiuchi, Takao; Takeda, Yasuyuki; Haginoya, Noriyasu; Miyazaki, Masaki; Nagata, Motoko; Kitagawa, Mayumi; Akahane, Kouichi; Uoto, Kouichi published the artcile< Discovery of novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based cyclin-dependent kinase 4 inhibitors: synthesis, biological evaluation and structure-activity relationships>, Recommanded Product: Thiazole-5-carboxyaldehyde, the main research area is thienopyrimidinyl hydrazone preparation biol activity cyclin dependent kinase inhibitor; anticancer agent thienopyrimidinyl hydrazone preparation structure activity relationship; structure activity relationship thienopyrimidinyl hydrazone preparation CDK4 inhibitor.

The design, synthesis, and evaluation of novel thieno[2,3-d]pyrimidin-4-yl hydrazones, e.g. I, as cyclin-dependent kinase 4 (CDK4) inhibitors are described. In continuing our program aim to search for potent CDK4 inhibitors, the introduction of a thiazole group at the hydrazone part has led to marked enhancement of chem. stability. Furthermore, by focusing on the optimization at the C-4′ position of the thiazole ring and the C-6 position of the thieno[2,3-d]pyrimidine moiety, compound I has been identified with efficacy in a xenograft model of HCT116 cells. In this paper, the potency, selectivity profile, and structure-activity relationships of our synthetic compounds are discussed.

Chemical & Pharmaceutical Bulletin 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

Isbrandt, Eric S.; Nasim, Amrah; Zhao, Karen; Newman, Stephen G. published the artcile< Catalytic Aldehyde and Alcohol Arylation Reactions Facilitated by a 1,5-Diaza-3,7-diphosphacyclooctane Ligand>, Related Products of 1003-32-3, the main research area is aryl iodide aldehyde nickel diazadiphosphacyclooctane catalyst reductive Heck arylation; primary alc aryliodide nickel diazadiphosphacyclooctane catalyst reductive Heck arylation; secondary alc preparation.

A catalytic method to access secondary alcs. by the coupling of aryl iodides was reported. Either aldehydes or alcs. can be used as reaction partners, making the transformation reductive or redox-neutral, resp. The reaction was mediated by a Ni catalyst and a 1,5-diaza-3,7-diphosphacyclooctane. This P2N2 ligand, which was previously been unrecognized in cross-coupling and related reactions, was found to avoid deleterious aryl halide reduction pathways that dominate with more traditional phosphines and NHCs. An interrupted carbonyl-Heck type mechanism was proposed to be operative, with a key 1,2-insertion step forging the new C-C bond and forming a nickel alkoxide that may be turned over by an alc. reductant. The same catalyst was also found to enable synthesis of ketone products from either aldehydes or alcs., demonstrating control over the oxidation state of both the starting materials and products.

Journal of the American Chemical Society published new progress about Aldehydes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Related Products of 1003-32-3.

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