Category: benzoxazole

Murray, Christopher W.; Berdini, Valerio; Buck, Ildiko M.; Carr, Maria E.; Cleasby, Anne; Coyle, Joseph E.; Curry, Jayne E.; Day, James E. H.; Day, Phillip J.; Hearn, Keisha; Iqbal, Aman; Lee, Lydia Y. W.; Martins, Vanessa; Mortenson, Paul N.; Munck, Joanne M.; Page, Lee W.; Patel, Sahil; Roomans, Susan; Smith, Kirsten; Tamanini, Emiliano; Saxty, Gordon published the artcile< Fragment-Based Discovery of Potent and Selective DDR1/2 Inhibitors>, Safety of 5-Fluorobenzo[d]oxazole-2-thiol, the main research area is DDR inhibitor antitumor oral; back to front kinase design; discoidin domain receptor; fragment-based drug design.

The DDR1 and DDR2 receptor tyrosine kinases are activated by extracellular collagen and have been implicated in a number of human diseases including cancer. We performed a fragment-based screen against DDR1 and identified fragments that bound either at the hinge or in the back pocket associated with the DFG-out conformation of the kinase. Modeling based on crystal structures of potent kinase inhibitors facilitated the “”back-to-front”” design of potent DDR1/2 inhibitors that incorporated one of the DFG-out fragments. Further optimization led to low nanomolar, orally bioavailable inhibitors that were selective for DDR1 and DDR2. The inhibitors were shown to potently inhibit DDR2 activity in cells but in contrast to unselective inhibitors such as dasatinib, they did not inhibit proliferation of mutant DDR2 lung SCC cell lines.

ACS Medicinal Chemistry Letters published new progress about Conformation. 13451-78-0 belongs to class benzoxazole, and the molecular formula is C7H4FNOS, Safety of 5-Fluorobenzo[d]oxazole-2-thiol.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Guang-cheng; Wang, Jing; Li, Lu-yao; Chen, Shan; Peng, Ya-ping; Xie, Zhen-zhen; Chen, Ming; Deng, Bin; Li, Wen-biao published the artcile< Synthesis of N-aryl-2-aminobenzoxazoles from substituted benzoxazole-2-thiol and 2-chloro-N-arylacetamides in KOH-DMF system>, HPLC of Formula: 13451-78-0, the main research area is aminobenzoxazole aryl preparation; benzoxazole thiol arylacetamide chloro condensation.

A simple and novel method for the synthesis of N-aryl-2-aminobenzoxazoles I [R1 = H, 5-F, 6-Me, etc. ; R2 = 4-Cl, 2,4-di-Me, 4-OPh, etc.] from substituted benzoxazole-2-thiols II and 2-chloro-N-arylacetamides R2C6H4NHC(O)CH2Cl in KOH-DMF system has been developed. The present protocol provides an attractive approach to access various N-aryl-2-aminobenzoxazoles I in moderate to good yields without using transition metal catalyst under very mild reaction condition.

Heterocycles published new progress about Acetamides Role: RCT (Reactant), RACT (Reactant or Reagent). 13451-78-0 belongs to class benzoxazole, and the molecular formula is C7H4FNOS, HPLC of Formula: 13451-78-0.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Paun, Anca; Matache, Mihaela; Enache, Florina; Nicolau, Ioana; Paraschivescu, Codruta C.; Ionita, Petre; Zarafu, Irina; Parvulescu, Vasile I.; Guillaumet, Gerald published the artcile< Convenient synthesis of 2-alkynylbenzazoles through Sonogashira cross-coupling reaction between thioethers and terminal alkynes>, COA of Formula: C7H4FNOS, the main research area is alkynylbenzoxazole alkynylbenzothiazole preparation; heteroaryl thioether terminal alkyne Sonogashira cross coupling.

Synthesis of 2-alkynylbenzoxazole and 2-alkynylbenzothiazole derivatives, e.g., I and II resp., via Sonogashira cross-coupling reaction of the corresponding thioethers and terminal alkynes under aerobic conditions, using CuI and Pd(dppf)Cl2 as catalysts was described. This synthetic methodol. allows the convenient cross-coupling of heteroaromatic substrates with a wide variety of aromatic and aliphatic alkynes, in moderate to good yields. The behavior of mercapto benzoxazoles and benzothiazoles were also investigated in the desulfitative Sonogashira cross-coupling reaction. It is noteworthy that the reaction occurred better under aerobic conditions rather than an inert atm., although with increased amounts of the diyne side-product.

Tetrahedron Letters published new progress about Alkynes, internal Role: SPN (Synthetic Preparation), PREP (Preparation). 13451-78-0 belongs to class benzoxazole, and the molecular formula is C7H4FNOS, COA of Formula: C7H4FNOS.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Mitra, Raja; Samuelson, Ashoka G. published the artcile< Substitution-Modulated Anticancer Activity of Half-Sandwich Ruthenium(II) Complexes with Heterocyclic Ancillary Ligands>, Application In Synthesis of 13451-78-0, the main research area is crystal mol structure cymeneruthenium mercaptobenzoxazole mercaptobenzothiazole mercaptobenzimidazole preparation anticancer.

Ten new organometallic half-sandwich Ru complexes with heterocyclic ligands were synthesized. The substituents on the ancillary heterocyclic ligands were varied to understand the effect of substitution on anticancer activity. The crystallog. characterization of five complexes confirms that they adopt three-legged piano-stool structures and are stabilized by intramol. H bonding. The two complexes with chloro- and bromo-substituted mercaptobenzothiazole ligands exhibit halogen bonding in the solid state. In aqueous media, the complexes form dinuclear Ru species. The complex with the noncytotoxic heterocycle, 6-fluoro-2-mercaptobenzothiazole, and the complex with the unsubstituted 2-mercaptobenzothiazole are the most active against A2780 and KB cell lines. The substitution of the H atoms on the ancillary ligand with Cl or Br atoms decreases the anticancer activity. With the exception of the F-substituted mercaptobenzoxazole ligand, the complexes with mercaptobenzoxazole ligands are inactive against all of the tested cell lines. Ru complexes with mercaptonaphthimidazole and mercaptobenzimidazole do not show any anticancer activity. The active complexes show a biphasic melting curve when incubated with calf thymus (CT) DNA. These complexes only inhibit thioredoxin reductase (TrxR) enzyme activity to a small extent. The substitution of H atoms with F atoms in the aromatic heterocyclic ligands on the organometallic half-sandwich Ru complexes has the most beneficial effect on their anticancer activity.

European Journal of Inorganic Chemistry published new progress about Antitumor agents. 13451-78-0 belongs to class benzoxazole, and the molecular formula is C7H4FNOS, Application In Synthesis of 13451-78-0.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yamazaki, Yukiyoshi; Abe, Kazutoyo; Toma, Tsutomu; Nishikawa, Masahiro; Ozawa, Hidefumi; Okuda, Ayumu; Araki, Takaaki; Oda, Soichi; Inoue, Keisuke; Shibuya, Kimiyuki; Staels, Bart; Fruchart, Jean-Charles published the artcile< Design and synthesis of highly potent and selective human peroxisome proliferator-activated receptor α agonists>, Reference of 13451-78-0, the main research area is aryloxyalkyl benzoxazole substituted aminoalkyl aryloxyalkanoic acid preparation PPAR agonist; structure aminoalkyl aryloxyalkanoic acid activity selectivity PPAR alpha agonist; hypolipemic activity PPAR binding selectivity aminoalkyl aryloxyalkanoic acid.

Aryloxyalkanoic acids substituted with aryloxyalkyl and benzoxazole-substituted aminoalkyl groups such as I are prepared as human peroxisome proliferator-activated receptor α (PPAR-α) agonists for decreasing lipid levels; the binding of the compounds to PPAR-α, PPAR-δ, and PPA-γ and the decreases in liver weight and triglyceride levels in rats upon administration of the sodium salts of three of the compounds are determined The racemate of I is prepared and resolved by HPLC to provide I and its enantiomer; I inhibits PPAR-α with an EC50 value of 1 nM and approx. 1000-fold selectivity over PPAR-δ and PPAR-γ, while the sodium salt of I decreases triglyceride concentrations in rats by approx. 49%.

Bioorganic & Medicinal Chemistry Letters published new progress about Apolipoprotein A-I Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 13451-78-0 belongs to class benzoxazole, and the molecular formula is C7H4FNOS, Reference of 13451-78-0.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Varun, Begur Vasanthkumar; Gadde, Karthik; Prabhu, Kandikere Ramaiah published the artcile< Sulfenylation of β-Diketones Using C-H Functionalization Strategy>, SDS of cas: 13451-78-0, the main research area is bezoxazolethione diketone sulfenylation cross dehydrogenative coupling; bezoxazolyl sulfenylated diketone preparation.

Sulfenylation of β-diketones is challenging as β-diketones undergo deacylation after sulfenylation in the reaction medium. The sulfenylation of β-diketones without deacylation under metal-free conditions at ambient temperature via a cross dehydrogenative coupling (CDC) strategy is reported. The resultant products can be further manipulated to form α,α-disubstituted β-diketones and pyrazoles.

Organic Letters published new progress about Diketones, 1,3-diketones Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 13451-78-0 belongs to class benzoxazole, and the molecular formula is C7H4FNOS, SDS of cas: 13451-78-0.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Sever, Belgin; Akalin Ciftci, Guelsen; Altintop, Mehlika Dilek published the artcile< A new series of benzoxazole-based SIRT1 modulators for targeted therapy of non-small-cell lung cancer>, Computed Properties of 13451-78-0, the main research area is NSCLC anticancer SIRT1 modulator mol docking apoptosis ADME; SIRT1; apoptosis; benzimidazole; benzoxazole; molecular docking; non-small-cell lung cancer.

In an attempt to identify potential anticancer agents for non-small-cell lung cancer (NSCLC) targeting sirtuin 1 (SIRT1), the synthesis of a new series of benzoxazoles (3a – i) was carried out through a facile and versatile synthetic route. The compounds were evaluated for their cytotoxic effects on A549 human lung adenocarcinoma and NIH/3T3 mouse embryonic fibroblast cells using the MTT assay. 2-[(5-Nitro-1H-benzimidazol-2-yl)thio]-N-(2-methylbenzoxazol-5-yl)acetamide (3e) and 2-[(5-chloro-1H-benzimidazol-2-yl)thio]-N-(2-methylbenzoxazol-5-yl)acetamide (3g) were the most potent and selective anticancer agents in this series against the A549 cell line, with IC50 values of 46.66 ± 11.54 and 55.00 ± 5.00μM, resp. The flow cytometry-based apoptosis detection assay was performed to determine their effects on apoptosis in A549 cells. Both compounds induced apoptosis in a dose-dependent manner. The effects of compounds 3e and 3g on SIRT1 activity were determined On the basis of in vitro studies, it was observed that compound 3g caused a significant decrease in SIRT1 levels in a dose-dependent manner, whereas compound 3e increased the SIRT1 levels. According to mol. docking studies, the substantial alteration in the type of action could be attributed to the difference between the interactions of compounds 3e and 3g with the same residues in the active site of SIRT1 (PDB code: 4IG9). On the basis of in silico ADME (absorption, distribution, metabolism, and excretion) studies, these compounds are predicted to possess favorable ADME profiles. According to the in vitro and in silico studies, compounds 3e and 3g, small-mol. SIRT1 modulators, were identified as potential orally bioavailable anticancer agents for the targeted therapy of NSCLC.

Archiv der Pharmazie (Weinheim, Germany) published new progress about Antitumor agents. 13451-78-0 belongs to class benzoxazole, and the molecular formula is C7H4FNOS, Computed Properties of 13451-78-0.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Liu, Xing; Zhang, Shi-Bo; Dong, Zhi-Bing published the artcile< AlCl3-Promoted Synthesis of 2-Mercapto Benzoheterocycles by Using Sodium Dimethyldithiocarbamate as Thiocarbonyl Surrogate>, COA of Formula: C7H4FNOS, the main research area is arylamine dimethyldithiocarbamate cyclization aluminum; mercaptobenzothiazole preparation; mercaptobenzoxazole preparation; mercaptobenzimidazole preparation; aluminum cyclization catalyst.

A simple, expeditious and high-efficiency synthetic method for the AlCl3-mediated one-pot preparation of 2-mercaptobenzoheterocycles (2-mercaptobenzothiazoles, -benzoxazoles and -benzimidazoles) is described. By the treatment of a series of S, O and N heteroatoms containing bifunctional mols. with sodium dimethyldithiocarbamate in AlCl3, the desired benzoheterocycles are obtained smoothly. The protocol can also be applied on the synthesis of a series of thiazolidine-2-thiones, imidazolidine-2-thiones. This synthetic approach has advantages such as ligand-free, high efficiency, short reaction time, readily available starting materials and simple exptl. procedures.

European Journal of Organic Chemistry published new progress about Aromatic amines Role: RCT (Reactant), RACT (Reactant or Reagent). 13451-78-0 belongs to class benzoxazole, and the molecular formula is C7H4FNOS, COA of Formula: C7H4FNOS.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Altintop, Mehlika Dilek; Akalin Ciftci, Gulsen; Temel, Halide Edip published the artcile< Synthesis and evaluation of new benzoxazole derivatives as potential antiglioma agents>, HPLC of Formula: 13451-78-0, the main research area is benzoxazole based hydrazone preparation human apoptosis pharmacokinetics antiglioma.

New benzoxazole-based hydrazone derivatives I [R = H, F, Ph, etc.] were designed, synthesized and investigated against cytotoxic effects on C6 rat glioma and NIH/3T3 mouse embryonic fibroblast cell lines using MTT assay. The apoptotic effects of the most selective anticancer agent were analyzed based on Annexin V-PI binding capacities in flow cytometry. The compounds I were also investigated for their acetylcholinesterase (AChE) inhibitory effects using a modification of Ellman’s spectrophotometric method. In order to evaluate the compliance of the compounds to Lipinski’s rule of five, their physicochem. parameters were determined using Molinspiration software. Compound I [R = Ph] was found to be more effective on C6 cell line (IC50 = 4.30 ± 0.28 μg/mL) than mitoxantrone (IC50 = 4.56 ± 1.24 μg/mL). The high SI value of compound I [R = Ph] indicated that its antiglioma activity was selective. This compound caused late apoptosis in a dose dependent manner. Compound I [R = Ph] was also found to be the most effective AChE inhibitor in this series. According to in silico studies, compound I [R = Ph] only violated one parameter of Lipinski’s rule of five. On the basis of Lipinski’s rule, the compound was expected to have reasonable oral bioavailability.

Marmara Pharmaceutical Journal published new progress about Antitumor agents. 13451-78-0 belongs to class benzoxazole, and the molecular formula is C7H4FNOS, HPLC of Formula: 13451-78-0.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zhu, Kai; Wang, Yi; Fang, Qi; Song, Zongqiang; Zhang, Fengzhi published the artcile< Enantioselective Synthesis of Axially Chiral Biaryls via Copper-Catalyzed Thiolation of Cyclic Diaryliodonium Salts>, Recommanded Product: 5-Fluorobenzo[d]oxazole-2-thiol, the main research area is iodo alkyl biphenyl thio benzoxazole preparation enantioselective; cyclic diaryliodonium salt mercaptobenzoxazole thiolation chiral copper catalyst; benzothiazole thio iodo alkyl biphenyl preparation enantioselective; mercaptobenzothiazole cyclic diaryliodonium salt thiolation chiral copper catalyst.

A chiral copper(II)-bisoxazoline-catalyzed enantioselective ring opening of cyclic diaryliodonium salts with heteroaryl thiols to give 2-((2′-iodo-6,6′-alkyl-[1,1′-biphenyl]-2-yl)thio)-5-benzo[d]oxazoles and 2-((2′-iodo-6,6′-alkyl-[1,1′-biphenyl]-2-yl)thio)-5-benzo[d]thiazoles I [R1 = 6-Me, 6-Cl, 6-OH, etc.; R2 = 6-Me, 6-Cl, 4.6-Me2, etc.; R3 = 2-pyridyl, 2-mercaptobenzoxazolyl, 5-Cl-mercaptobenzoxazol-2-yl, etc.] in excellent yields and enantioselectivities was reported. The products were further transformed into diverse enantiopure alkyl biaryl sulfides I [R1 = 6-Me; R2 = 6-Me; R3 = Me, i-Pr, Bn, etc.] which could be employed as chiral ligands.

Organic Letters published new progress about Benzothiazoles Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 13451-78-0 belongs to class benzoxazole, and the molecular formula is C7H4FNOS, Recommanded Product: 5-Fluorobenzo[d]oxazole-2-thiol.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem