6248-20-0

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Uses

4-Formyl-2-methylresorcinol is a reactant in the synthesis of 3-benzo[b]thiophenecoumarin, with potent anti-proliferative activity against breast cancer cell lines

InChI:InChI=1/C8H8O3/c1-5-7(10)3-2-6(4-9)8(5)11/h2-4,10-11H,1H3

Upstream product

• 608-25-3 2-methylbenzene-1,3-diol 
• 557-21-1 dicyanozinc 
• 68-12-2 N,N-dimethyl-formamide 
• 6971-52-4 3-methoxy-2-methylphenol 
• 557-21-1 zinc(II) cyanide 
• 93-61-8 N-methyl-N-phenylformamide 
• 634-65-1 2,4-dimethylbenzene-1,3-diol 

Downstream Products

• 35499-90-2 7-hydroxy-8-methyl-2-phenyl-chromenylium; chloride 
• 219298-64-3 2-methoxy-3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde 
• 219298-63-2 2-hydroxy-3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde 
• 914399-70-5 2-hydroxy-4-(methoxymethoxy)-3-methylbenzaldehyde 
• 1361199-00-9 C₁₇H₁₁F₃O₄ 
• 1361198-99-3 C₁₆H₁₁FO₃ 
• 1361198-98-2 C₁₆H₁₁ClO₃ 
• 1361198-97-1 C₁₇H₁₄O₄ 
• 1361198-96-0 C₁₆H₁₂O₃ 
• 1361199-30-5 8-methyl-7-((1-methylpiperidin-4-yl)oxy)-3-(4-(trifluoromethoxy)phenyl)-2H-chromen- 
• 1361199-29-2 3-(4-fluorophenyl)-8-methyl-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one 
• 1361199-28-1 3-(4-chlorophenyl)-8-methyl-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one 
• 1361199-27-0 3-(4-methoxyphenyl)-8-methyl-7-((1-methylpiperidin-4-yl)oxy)-2H-chromen-2-one 

Relevant academic research and scientific papers

Cell-specific activation of gemcitabine by endogenous H2S stimulation and tracking through simultaneous fluorescence turn-on

The endogenous H2S-driven theranosticH2S-Gemhas been invented. The theranostic prodrugH2S-Gemis selectively activated in cancer cells, releasing active gemcitabine with a simultaneous fluorescence turn-on.H2S-Gemselectively inhibited cancer cell growth compared to the mother chemotherapeutic gemcitabine. Overall, it is a unique protocol for tracking and transporting chemotherapeutic agents to tumor areas without the guidance of tumor-directive ligands.

Rational drug design of benzothiazole-based derivatives as potent signal transducer and activator of transcription 3 (STAT3) signaling pathway inhibitors

The cumulative evidence supports STAT3, a transcriptional mediator of oncogenic signaling, as a therapeutic target in cancer. The development of STAT3 inhibitors remain an active area of research as no inhibitors have yet to be approved for cancer treatment. In a continuing effort to develop more potent STAT3 inhibitors based on our previously identified hit compound 16w, a series of benzothiazole derivatives with unique binding mode in SH2 domain of STAT3 were designed, synthesized and biologically evaluated. Of note, compound B19 demonstrated excellent activity against IL-6/STAT3 signaling pathway with the IC50 value as low as 0.067 μM as determined by a luciferase reporter assay. Moreover, multiple compounds displayed potent antiproliferative activity against MDA-MB-468 and JAK2 mutant HEL cell lines. Further biochemical study using Western blot assay indicated that B19 blocked the phosphorylation of STAT3 at Tyr 705 and Ser 727 and thus suppressed STAT3-mediated gene expression of c-MYC and MCL-1. Simultaneously, it induced cancer cell G2/M phase arrest and apoptosis both in MDA-MB-468 and HEL cell lines. Finally, molecular docking study along with surface plasmon resonance (SPR) and fluorescence polarization (FP) assays disclosed the binding mode of B19 in STAT3 SH2 domain. Taken together, our finding suggests that B19 is a promising therapeutic STAT3 inhibitor for cancer treatment.

Exploring boron applications in modern agriculture: A structure-activity relationship study of a novel series of multi-substitution benzoxaboroles for identification of potential fungicides

Several boron-containing small molecules have been approved by the US FDA to treat human diseases. We explored potential applications of boron-containing compounds in modern agriculture by pursuing multiple research and development programs. Here, we report a novel series of multi-substitution benzoxaboroles (1–36), a compound class that we recently reported as targeting geranylgeranyl transferase I (GGTase I) and thereby inhibiting protein prenylation (Kim et al., 2020). These compounds were designed, synthesized, and tested against the agriculturally important fungal pathogens Mycosphaerella fijiensis and Colletotrichum sublineolum in a structure–activity relationship (SAR) study. Compounds 13, 28, 30, 34 and 36 were identified as active leads with excellent antifungal MIC95 values in the range of 1.56–3.13 ppm against M. fijiensis and 0.78–3.13 ppm against C. sublineolum.

BORON CONTAINING COMPOUNDS AND THEIR USES

The present disclosure contemplates novel boron-containing compounds and their uses as active agents that exhibit pesticidal activity such as antimicrobial, insecticidal, arachnicidal, and/or anti parasitic activity. An agrochemical composition containing such a compound and its use in, animal health, agriculture, or horticulture is also contemplated. A method for promoting plant performance and/or controlling, reducing, preventing, ameliorating, or inhibiting microbes, insects, arachnids, and/or parasites on or in an animal, a plant, a plant part, plant propagation material, and/or harvested fruits or vegetables is also contemplated.

Bypassing Biocatalytic Substrate Limitations in Oxidative Dearomatization Reactions by Transient Substrate Mimicking

Enzymatic oxidative dearomatization is an efficient way to generate chiral molecules from simple arenes. One example is the flavin-dependent monooxygenase SorbC involved in sorbicillinoid biosynthesis. However, SorbC requires a long-chain keto substituent at its phenolic substrate, thus preventing its application beyond the synthesis of natural sorbicillinoids or close structural analogues. This work describes an approach to broaden the accessible product spectrum of SorbC by employing an ester functionality mimicking the natural substrate structure during enzymatic oxidation.

(S)-N-(1-phenethyl) thioacetamide compound as well as medicinal composition and application thereof

The invention belongs to the field of medicinal chemicals, relates to a STAT3 inhibitor, and in particular to a (S)-N-(1-phenethyl) thioacetamide compound of a structure of formula (I) as shown in the specification, a medicinal composition of the compound as an STAT3 (Signal Transducer and Activator of Transcription 3) signal path inhibitor, and application of the compound in preparing anti-tumor medicines. Results of cell experiment show that the compound targets a Phe-Lys-Thr-Lys-Leu pentapeptide binding region in an STAT3 SH2 structure domain, then inhibits STAT3 protein monomer dimerization and silencing STAT3 signal transduction and functions, has a remarkable anti-tumor effect and good physical and chemical properties, is particularly capable of effectively preventing cell proliferative activity in breast cancer cells with high expression of STAT3 and HEL cells on which JAK2/STAT3 signal paths depend with JAK2 V671F mutation, and moreover is capable of effectively inhibiting phosphorylation of STAT3 in the breast cancer cells with high expression of STAT3 and expression of downstream target genes such as CyclinD1 and Bc1-2.

Stereoselective Total Synthesis of Bisorbicillinoid Natural Products by Enzymatic Oxidative Dearomatization/Dimerization

Natural products are a virtually inexhaustible source of small molecules with spectacular molecular architectures and biomedical potential. Their structural complexity generates formidable challenges to total synthesis but often also precludes time- and resource-efficient, stereoselective synthetic access. Biosynthetically, nature frequently uses dimerization and oligomerization reactions to produce highly challenging frameworks from simple starting materials. Impressive examples are the bisorbicillinoids, a family of fungal natural products thought to originate from the polyketide precursor sorbicillin. Utilizing the recombinant oxidoreductase SorbC from the sorbicillin biosynthetic gene cluster, a robust, fully stereoselective synthesis of bisorbicillinoid natural products and unnatural side-chain analogues was developed.

Benzoxaborole Antimalarial Agents. Part 5. Lead Optimization of Novel Amide Pyrazinyloxy Benzoxaboroles and Identification of a Preclinical Candidate

Carboxamide pyrazinyloxy benzoxaboroles were investigated with the goal to identify a molecule with satisfactory antimalarial activity, physicochemical properties, pharmacokinetic profile, in vivo efficacy, and safety profile. This optimization effort discovered 46, which met our target candidate profile. Compound 46 had excellent activity against cultured Plasmodium falciparum, and in vivo against P. falciparum and P. berghei in infected mice. It exhibited good PK properties in mice, rats, and dogs. It was highly active against the other 11 P. falciparum strains, which are mostly resistant to chloroquine and pyrimethamine. The rapid parasite in vitro reduction and in vivo parasite clearance profile of 46 were similar to those of artemisinin and chloroquine, two rapid-acting antimalarials. It was nongenotoxic in an Ames assay, an in vitro micronucleus assay, and an in vivo rat micronucleus assay when dosed orally up to 2000 mg/kg. The combined properties of this novel benzoxaborole support its progression to preclinical development.

PROCESS FOR THE PREPARATION OF 2-SUBSTITUTED-2-(6-(SUBSTITUTED)-7-METHYLBENZO[D][1,3]DIOXOL-4-YL)ACETIC ACID DERIVATIVES

Present invention relates to an improved and commercial process for the preparation of 2-sustituted-2-(6-(substituted)-7-methylbenzo[d][1,3]dioxol-4-yl)acetic acid derivatives of formula-I [Formula should be inserted here], wherein R1 is a O-protecting group such as methoxymethyl, ethoxymethyl, trialkylsilyl, arylmethyl, tetrahydropyran-2-yl, allyl; X is hydroxyl, halogen, mesylate, triflate, tosylate, acetate; Y is oxygen atom, NH or sulfur atom; R2 is C1-C6 alkyl. 2,4-Dihydroxy-3-methylbenzal-dehyde is selectively protected at C-4 position in the form of an ether compound of formula-XII, oxidized the aldehyde function to get the diol of formula-XIII, and condensed with ethyl glyoxalate under Casiraghi reaction conditions to get the compound of formula-XV. Compound of formula-XV is converted to compound of formula-I by conventional chemistry. Compounds of formula-I are key intermediates in the synthesis of ecteinascidines like trabectedin

1 -HYDROXY-BENZOOXABOROLES AS ANTIPARASITIC AGENTS

Provided are compounds useful for controlling endoparasites both in animals and agriculture. Further provided are methods for controlling endoparasite infestations of an animal by administering an effective amount of a compound as described above, or a pharmaceutically acceptable salt thereof, to an animal, as well as formulations for controlling endoparasite infestations using the compounds described above or an acceptable salt thereof, and an acceptable carrier. The claimed compounds are described by the following Markush formula:A typical example for a compound according to above formula is: A typical example for a compound according to above formula is: