Heterocyclic Building Blocks-Thiomorpholine

Lamers, Philip published the artcileTetrahydrobenzo[c]thieno[2,1-e]isothiazole 4-Oxides: Three-Dimensional Heterocycles as Cross-Coupling Building Blocks, Quality Control of 220655-09-4, the main research area is benzothienoisothiazole oxide preparation; oxidative arylation tetrahydrothiophene aniline oxidative cyclocondensation; borylation coupling reaction bromo iodo benzothienoisothiazole oxide.

Tetrahydrobenzothienoisothiazole oxides such as I (R = H, I, Br, F, Cl, NC, MeO2C, O2N, F5S, F3C), cyclic sulfoximines, were prepared as novel heterocycles amenable to cross-coupling reactions and automated parallel synthesis. Reaction of tetrahydrothiophene with anilines such as 4-RC6H4NH2 (R = H, I, Br, F, Cl, NC, MeO2C, O2N, F5S, F3C) mediated by N-chlorosuccinimide (NCS) and Et3N in CH2Cl2 yielded (tetrahydrothienyl)anilines such as II (R = H, I, Br, F, Cl, NC, MeO2C, O2N, F5S, F3C) in 29-89% yields; tetrahydrothiopyran, N-Boc thiomorpholine, and 1,4-thioxane yielded thioether-substituted anilines, but the products did not undergo oxidative cyclocondensation. Further oxidation of (tetrahydrothienyl)anilines with N-chlorosuccinimide, treatment with aqueous NaOH, and oxidation with meta-chloroperbenzoic acid (mCPBA) yielded such as I (R = H, I, Br, F, Cl, NC, MeO2C, O2N, F5S, F3C). I (R = I, Br) and related tetrahydrobenzothienoisothiazole oxides underwent borylation, Sonogashira, and Suzuki coupling reactions.

Organic Letters published new progress about Arylation. 220655-09-4 belongs to class thiomorpholine, name is tert-Butyl thiomorpholine-4-carboxylate, and the molecular formula is C9H17NO2S, Quality Control of 220655-09-4.

Referemce:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Kamijo, Shin published the artcilePhoto-induced Substitutive Introduction of the Aldoxime Functional Group to Carbon Chains: A Formal Formylation of Non-Acidic C(sp3)-H Bonds, Name: tert-Butyl thiomorpholine-4-carboxylate, the main research area is formylation carbon hydrogen bond arylsulfonyl oxime; 4-benzoylpyridine; C−H functionalization; aldoximes; photoreactions; radicals.

A photo-induced substitutive introduction of an aldoxime functional group to carbon chains was achieved using photo-excited 4-benzoylpyridine as a C(sp3)-H bond cleaving agent and arylsulfonyl oxime as an aldoxime precursor. The non-acidic C-H bonds in various substances, including cycloalkanes, ethers, azacycles, and cyclic sulfides, were chemoselectively converted at ambient temperature under neutral conditions. The present transformation is a formal formylation of non-acidic C(sp3)-H bonds in a single step.

Angewandte Chemie, International Edition published new progress about C-H bond cleavage. 220655-09-4 belongs to class thiomorpholine, name is tert-Butyl thiomorpholine-4-carboxylate, and the molecular formula is C9H17NO2S, Name: tert-Butyl thiomorpholine-4-carboxylate.

Referemce:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Grainger, Rachel published the artcileEnabling synthesis in fragment-based drug discovery by reactivity mapping: photoredox-mediated cross-dehydrogenative heteroarylation of cyclic amines, Application In Synthesis of 220655-09-4, the main research area is drug discovery cyclic amine photoredox cross dehydrogenative heteroarylation.

In fragment-based drug discovery (FBDD), a weakly binding fragment hit is elaborated into a potent ligand by bespoke functionalization along specific directions (growth vectors) from the fragment core in order to complement the 3D structure of the target protein. This structure-based design approach can present significant synthetic challenges, as growth vectors often originate on sp2 or sp3 ring carbons which are not the most synthetically accessible points on the fragment. To address this issue and expedite synthesis in FBDD, we established a nanogram-to-gram workflow for the development of enabling synthetic transformations, such as the direct C-H functionalization of heterocycles. This novel approach deploys high-throughput experimentation (HTE) in 1536-well microtiter plates (MTPs) facilitated by liquid handling robots to screen reaction conditions on the nanomolar scale; subsequently the reaction is upscaled in a continuous flow to generate gram-quantities of the material. In this paper, we disclose the use of this powerful workflow for the development of a photoredox-mediated cross-dehydrogenative coupling of fragments and medicinally relevant heterocyclic precursors via Minisci-type addition of a-amino radicals to electron-deficient heteroarenes. The optimized reaction conditions were employed on the milligram-scale on a diverse set of 112 substrates to map out structure-reactivity relationships (SRRs) of the transformation. The coupling exhibits excellent tolerance to a variety of functional groups and N-rich heteroarenes relevant to FBDD and was upscaled in a continuous flow to afford gram-quantities of pharmaceutically relevant sp2-sp3 privileged architectures.

Chemical Science published new progress about Drug discovery. 220655-09-4 belongs to class thiomorpholine, name is tert-Butyl thiomorpholine-4-carboxylate, and the molecular formula is C9H17NO2S, Application In Synthesis of 220655-09-4.

Referemce:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Alfonzo, Edwin published the artcilePhotoredox and Weak Bronsted Base Dual Catalysis: Alkylation of α-Thio Alkyl Radicals, Product Details of C9H17NO2S, the main research area is radical alkylation thioether photoredox Bronsted base dual catalysis.

We report the C-H activation of thioethers to α-thio alkyl radicals and their addition to electron-deficient olefins to afford alkylated products through dual photoredox and weak Bronsted base catalysis. Mechanistic studies are consistent with a two-step activation mechanism, where oxidation of thioethers to their corresponding sulfide radical cations by an acridinium photoredox catalyst is followed with deprotonation by trifluoroacetate to generate α-thio alkyl radicals and trifluoroacetic acid (TFA). Exptl. studies support the involvement of TFA in all subsequent steps leading to product formation.

ACS Catalysis published new progress about Alkenes, electron-deficient Role: RCT (Reactant), RACT (Reactant or Reagent). 220655-09-4 belongs to class thiomorpholine, name is tert-Butyl thiomorpholine-4-carboxylate, and the molecular formula is C9H17NO2S, Product Details of C9H17NO2S.

Referemce:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Wu, Yachuang published the artcileOptimization of biaryloxazolidinone as promising antibacterial agents against antibiotic-susceptible and antibiotic-resistant gram-positive bacteria, Safety of tert-Butyl thiomorpholine-4-carboxylate, the main research area is biaryloxazolidinone preparation antibacterial; Antibiotic-resistant infections; Biaryloxazolidinone; Gram-positive bacteria; Structural optimization.

Herein, novel biaryloxazolidinone analogs I [X = O, S, NMe, etc.; Y = N, CH, CHOH, etc.; Z = N, CH] were designed and synthesized to improve the chem. and metabolic stability. Compounds I [X = S, NMe, SO2; Y = N, CHOH; Z = CH] showed significant antibacterial activity against the tested Gram-pos. bacteria as compared to radezolid and linezolid. Further studies indicated that most of them exhibited improved water solubility and chem. stability. Compound I [X = SO2; Y = N; Z = CH] had MIC values of 0.125-0.25 μg/mL against all tested Gram-pos. bacteria, and showed excellent antibacterial activity against clin. isolates of antibiotic-susceptible and antibiotic-resistant bacteria. Moreover, it was stable in human liver microsome. From a safety viewpoint, it showed non-cytotoxic activity against hepatic cell and exhibited lower inhibitory activity against human MAO-A compared to linezolid. The potent antibacterial activity and all these improved drug-likeness properties and safety profile suggested that compound I [X = SO2; Y = N; Z = CH] might be a promising drug candidate for further investigation.

European Journal of Medicinal Chemistry published new progress about Acid chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 220655-09-4 belongs to class thiomorpholine, name is tert-Butyl thiomorpholine-4-carboxylate, and the molecular formula is C9H17NO2S, Safety of tert-Butyl thiomorpholine-4-carboxylate.

Referemce:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Alfonzo, Edwin published the artcileα-Heteroarylation of Thioethers via Photoredox and Weak Bronsted Base Catalysis, HPLC of Formula: 220655-09-4, the main research area is Heteroarylation thioether photoredox weak Bronsted base catalysis; Classical Minisci Reaction with Thioethers.

We report the C-H activation of thioethers to α-thio alkyl radicals and their addition to N-methoxyheteroarenium salts for the redox-neutral synthesis of α-heteroaromatic thioethers. Studies are consistent with a two-step activation mechanism, where oxidation of thioethers to sulfide radical cations by a photoredox catalyst is followed by α-C-H deprotonation by a weak Bronsted base catalyst to afford α-thio alkyl radicals. Further, N-methoxyheteroarenium salts play addnl. roles as a source of methoxyl radical that contributes to α-thio alkyl radical generation and a sacrificial oxidant that regenerates the photoredox catalytic cycle.

Organic Letters published new progress about Bronsted bases Role: CAT (Catalyst Use), USES (Uses). 220655-09-4 belongs to class thiomorpholine, name is tert-Butyl thiomorpholine-4-carboxylate, and the molecular formula is C9H17NO2S, HPLC of Formula: 220655-09-4.

Referemce:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Kumaraswamy, B. published the artcileSynthesis, characterization and in vitro antimicrobial evaluation of some new amides of thiomorpholine carboxylate, Application of tert-Butyl thiomorpholine-4-carboxylate, the main research area is thiomorpholine carboxylate dioxide amide preparation antibacterial antifungal.

Synthesis and antimicrobial evaluation of some new amides of Thiomorpholine caboxylate is described. A series of new amides of Thiomorpholine caboxylate were synthesized by reacting 4-tert-Bu 2-Me thiomorpholine-2,4-dicarboxylate 1,1-dioxide with primary amines in presence of Tri-Me aluminum in toluene at ambient temperature in good yields. 4-Tert-Bu 2-Me thiomorpholine-2,4-dicarboxylate 1,1-dioxide was synthesized by reacting tert-Bu thiomorpholine-4-carboxylate 1,1-dioxide with Me chloroformate in presence of LiHMDS (1M in THF) at -78° for the first time. The newly synthesized compounds were characterized by IR, 1HNMR, 13C NMR, Mass spectral studies and elemental anal. Preliminary results revealed that the synthesized compounds were showed moderate to good antibacterial and antifungal activity.

International Journal of Pharmacy and Pharmaceutical Sciences published new progress about Antibacterial agents. 220655-09-4 belongs to class thiomorpholine, name is tert-Butyl thiomorpholine-4-carboxylate, and the molecular formula is C9H17NO2S, Application of tert-Butyl thiomorpholine-4-carboxylate.

Referemce:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Colas, Kilian published the artcileIntermolecular Pummerer Coupling with Carbon Nucleophiles in Non-Electrophilic Media, Related Products of thiomorpholine, the main research area is intermol Pummerer coupling sulfoxide turbo organomagnesium amide; C−C coupling; Pummerer reaction; magnesium; main group elements; sulfur.

A new Pummerer-type C-C coupling protocol is introduced based on turbo-organomagnesium amides, which unlike traditional Pummerer reactions, does not require strong electrophilic activators, engages a broad range of C(sp3)-, C(sp2)-, and C(sp)-nucleophiles, and seamlessly integrates with C-H and C-X magnesiation. Given the central character of sulfur compounds in organic chem., this protocol allows access to unrelated carbonyls, olefins, organometallics, halides, and boronic esters through a single strategy.

Angewandte Chemie, International Edition published new progress about Grignard reagents. 220655-09-4 belongs to class thiomorpholine, name is tert-Butyl thiomorpholine-4-carboxylate, and the molecular formula is C9H17NO2S, Related Products of thiomorpholine.

Referemce:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Battula, Kumara Swamy published the artcileSynthesis and Biological Evaluation of Novel Thiomorpholine 1,1-Dioxide Derived 1,2,3-Triazole Hybrids as Potential Anticancer Agents, Recommanded Product: tert-Butyl thiomorpholine-4-carboxylate, the main research area is thiomorpholine triazole hybrid preparation antitumor human.

Synthesis and biol. evaluation of a new series of (4-((1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)(1,1-dioxidothiomorpholino)methanone derivatives I (R1 = 2-Me, 4-Cl, 2-MeO, etc.) has been described. The synthesized compounds were screened for in vitro anticancer activity against three cancer cell lines (MCF-7, HeLa, and HEK293) and compared with standard drug cisplatin. Among the fourteen derivatives, compounds I (R1 = 2-OMe, 3-OMe, 2-OH) exhibited potent anticancer activity against MCF-7, HeLa, and HEK293. Compounds I (R1 = 2-OMe, 3-OMe) were screened for in vivo studies against EAC bearing mice and found to possess potential anticancer activity.

ChemistrySelect published new progress about Antitumor agents. 220655-09-4 belongs to class thiomorpholine, name is tert-Butyl thiomorpholine-4-carboxylate, and the molecular formula is C9H17NO2S, Recommanded Product: tert-Butyl thiomorpholine-4-carboxylate.

Referemce:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem

Kalinin, Dmitrii V. published the artcileNovel Potent Proline-Based Metalloproteinase Inhibitors: Design, (Radio)Synthesis, and First in Vivo Evaluation as Radiotracers for Positron Emission Tomography, Formula: C9H17NO2S, the main research area is proline hydroxyproline hydroxamic acid synthesis metalloproteinase inhibitor structure activity; diagnostic agent PET tumor imaging radiotracer mol docking MMP; Sonogashira coupling alkylation acylation Mitsunobu reaction aminolysis fluorination; nucleophilic substitution protection radiotracer biodistribution pharmacokinetic.

As dysregulation of matrix metalloproteinase (MMP) activity is associated with a wide range of pathophysiol. processes like cancer, atherosclerosis, and arthritis, MMPs represent a valuable target for the development of new therapeutics and diagnostic tools. We herein present the chiral pool syntheses, in vitro evaluation and SAR studies of a series of D- and L-proline- as well as of (4R)-4-hydroxy-L-proline-derived MMP inhibitors. Some of the synthesized hydroxamic acids were found to be potent MMP inhibitors with IC50 values in the nanomolar range, also demonstrating no off-target effects towards the other tested Zn2+-dependent metalloproteases (ADAMs and meprins). Utilizing the structure of the (2S,4S)-configured 4-hydroxyproline derivative (I), a selective picomolar inhibitor of MMP-13, the radiolabeled counterpart [18F] was successfully synthesized. The radiotracer’s biodistribution in mice as well as its serum stability were evaluated for accessing its potential use as a MMP-13 targeting PET imaging agent.

Journal of Medicinal Chemistry published new progress about Acylation. 220655-09-4 belongs to class thiomorpholine, name is tert-Butyl thiomorpholine-4-carboxylate, and the molecular formula is C9H17NO2S, Formula: C9H17NO2S.

Referemce:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem