Tag: M.W=100-150

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

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

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

Subr, Vladimir; Ormsby, Tereza; Sacha, Pavel; Konvalinka, Jan; Etrych, Tomas; Kostka, Libor published the artcile< The role of the biotin linker in polymer antibody mimetics, iBodies, in biochemical assays>, Reference of 96-53-7, the main research area is biotin linker polymer antibody mimetics iBody biochem assay.

Recently, we have developed synthetic polymer-based antibody mimetics called iBodies that can successfully replace antibodies in many biochem. applications including ELISA (ELISA), flow cytometry, immunocytochem., affinity purification, and confocal microscopy. In this study, we focused primarily on the effect of a linker between the polymer backbone and biotin, and then on the influence of the number of biotins per polymer chain on the efficacy of the ELISA or pull-down assays. In addition, the biotin position on the polymer chain was investigated. Moreover, we developed a novel chain transfer agent suitable for RAFT polymerization, which enables the functionalization of specifically the polymer precursors and simplifies the synthesis of semitelechelic antibody mimetic materials. By employing optimized iBodies the sensitivity of the ELISA with a lengthened linker between the polymer backbone and biotin was increased up to 5 times. Importantly, we found that one biotin at the end of the polymer chain can replace up to 12 biotins located along the polymer chain and maintain the signal level in the ELISA, as well as in the pull-down assay.

Polymer Chemistry published new progress about Affinity purification. 96-53-7 belongs to class thiazole, and the molecular formula is C3H5NS2, Reference of 96-53-7.

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

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