Tag: M.W=150-200

Ellipilli, Satheesh published the artcileFluorinated peptide nucleic acids with fluoroacetyl side chain bearing 5-(F/CF₃)-uracil: Synthesis and cell uptake studies, COA of Formula: C4H6BrFO2, the publication is Journal of Organic Chemistry (2016), 81(15), 6364-6373, database is CAplus and MEDLINE.

Fluorine incorporation into organic mols. imparts favorable physicochem. properties such as lipophilicity, solubility and metabolic stability necessary for drug action. Toward such applications using peptide nucleic acids (PNA), we herein report the chem. synthesis of fluorinated PNA monomers and biophys. studies of derived PNA oligomers containing fluorine in in the acetyl side chain (-CHF-CO-) bearing nucleobase uracil (5-F/5-CF3-U). The crystal structures of fluorinated racemic PNA monomers reveal interesting base pairing of enantiomers and packing arrangements directed by the chiral F substituent. Reverse phase HPLC show higher hydrophobicity of fluorinated PNA oligomers, dependent on the number and site of the fluorine substitution: fluorine on carbon adjacent to the carbonyl group induces higher lipophilicity than fluorine on nucleobase or in the backbone. The PNA oligomers containing fluorinated bases form hybrids with cDNA/RNA with slightly lower stability compared to that of unmodified aeg PNA, perhaps due to electronic effects. The uptake of fluorinated homooligomeric PNAs by HeLa cells was as facile as that of nonfluorinated PNA. In conjunction with our previous work on PNAs fluorinated in backbone and at N-terminus, it is evident that the fluorinated PNAs have potential to emerge as a new class of PNA analogs for applications in functional inhibition of RNA.

Journal of Organic Chemistry published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C4H6BrFO2, COA of Formula: C4H6BrFO2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Zhao, Zhen-Zhen published the artcileNickel-Catalyzed Reductive C(sp²)-Si Coupling of Chlorohydrosilanes via Si-Cl Cleavage, Application In Synthesis of 111-83-1, the publication is Angewandte Chemie, International Edition (2022), 61(21), e202200215, database is CAplus and MEDLINE.

Authors report here a new method for the synthesis of organohydrosilanes from phenols and ketones. This method is established through reductive C-Si coupling of chlorohydrosilanes via unconventional Si-Cl cleavage. The reaction offers access to aryl- and alkenylhydrosilanes with a scope that is complementary to those of the established methods. Electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles, as well as cyclic and acyclic alkenyl electrophiles, were coupled successfully. Functionalities, including Grignard-sensitive groups (e.g., primary amine, amide, phenol, ketone, ester, and free indole), acid-sensitive groups (e.g., ketal and THP protection), alkyl-Cl, pyridine, furan, thiophene, Ar-Bpin, and Ar-SiMe₃, were tolerated. Gram-scale(coating) reaction, incorporation of -Si(H)R₂ into complex biol. active mols., and derivatization of formed organohydrosilanes are demonstrated.

Angewandte Chemie, International Edition published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C5H13Cl2N, Application In Synthesis of 111-83-1.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Forero-Doria, Oscar published the artcileNovel N-benzoylimidazolium ionic liquids derived from benzoic and hydroxybenzoic acids as therapeutic alternative against Biofilm-forming bacteria in skin and soft-tissue infections, Computed Properties of 111-83-1, the publication is Bioorganic Chemistry (2022), 105914, database is CAplus and MEDLINE.

The skin and soft tissue infections (SSTIs) -producing pathogens have acquired resistance to a wide range of antimicrobials, thus it is highly relevant to have new treatment alternatives. In this study, we report the synthesis, characterization, and antibacterial activity of three novel series of ionic liquids (ILs) derived from benzoic and hydroxybenzoic acids, with different lengths of the alkyl chain. The min. inhibitory concentration (MIC) were tested in Gram-pos.: Pseudomonas aeruginosa, Staphylococcus aureus, Staphylococcus epidermidis, and Streptococcus pyogenes, and Gram-neg.: Acinetobacter baumannii and Escherichia coli, showing a MIC range of 0.01562-2.0 mM, with the activity varying according to the aromatic ring functionalization and the length of the alkyl chains. Regarding the antibiofilm activity, different efficacy was observed among the different ILs, some of them presenting antibiofilm activities close to 80% as in the case of those derived from syringic acid with an alkyl chain of six carbon atoms against Pseudomonas aeruginosa. Furthermore, the cell viability in HaCaT cells was determined, showing a half maximal effective concentration (EC₅₀) values higher than the MIC values. The antimicrobial and antibiofilm results, along with not producing cellular toxicity at the MIC values shows that these ILs could be a promising alternative against SSTIs.

Bioorganic Chemistry published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Computed Properties of 111-83-1.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Stallberg, Gunnel published the artcileSynthesis and configuration of enantiometric β-bromoisobutyric acids, Safety of 3-Bromo-2-methylpropanoic acid, the publication is Arkiv foer Kemi (1957), 95-8, database is CAplus.

The enantiomeric β-bromoisobutyric acids could not be obtained by resolution of the inactive compound with brucine. They were, however, prepared by the Hunsdiecker degradation (C.A. 37, 3734⁴) of the enantiomeric half-esters of methyl succinic acid. Thus, to 0.047 mole (-)-Me 2L-methyl-3-carboxypropionate, neutralized with dilute NH₃, was added 0.049 mole aqueous AgNO₃ with cooling and stirring. After 3 hrs. the Ag salt (I) was filtered off, washed with water, MeOH, and Et₂O, and dried 48 hrs. at 90-5°. To 10.7 g. I in dry CCl₄ was added dry Br with cooling and shaking until the color persisted. After standing 6 hrs. at room temperature, the mixture was filtered, the filtrate washed with aqueous NaHCO₃ and water, dried, and fractionated yielding (+)-Me β-bromoisobutyrate (II), b₃₇ 85°, n²⁵_D 1.4532, d₂₅ 1.422, [α]²⁵_D 15.9° [M]²⁵_D 28.8°. II (4.9 g.) was refluxed 24 hrs. with 30 ml. AcOH containing 2 ml. 48% HBr and fractionated yielding (+)-β-bromoisobutyric acid, b_1.5 81.5°, n²⁵_D 1.4748, d₂₅ 1.579, [α]²⁵_D 10.5°, [M]²⁵_D 17.5°. Similarly, (+)-Me 2D-methyl-3-carboxypropionate was converted to (-)-Me β-bromoisobutyrate, b₁₂ 97.5-8.5°, n²⁵_D 1.4533, d₂₅ 1.422, [α]²⁵_D -15.9, and then to (-)-β-bromoisobutyric acid, b₂ 69-70°, n²⁵_D 1.4744, d₂₅ 1.576, [α]²⁵_D-10.5°.

Arkiv foer Kemi published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is C8H10O2, Safety of 3-Bromo-2-methylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Stallberg, Gunnel published the artcilePreparation of half-esters of alkylsuccinic acids with a free primary carboxyl group. Synthesis and optical configuration of optically active methyl 2-methyl-3-carboxypropanoate, Name: 3-Bromo-2-methylpropanoic acid, the publication is Acta Chemica Scandinavica (1956), 1360-1, database is CAplus.

The preparation of HO₂CCH₂CHMeCO₂Me (I), m. 42.2-2.8° (petr. ether), n²⁶_D 1.4309, [α]²⁵_D -9.3° (c 17.5, CHCl₃), made difficult by the simultaneous formation of HO₂CCHMeCH₂CO₂Me, is achieved in 60-8% yield by distilling the KMnO₄ oxidation product of CH₂:CHCH₂CHMeCO₂Me, b₇₆₀ 134.5-5.0°, n^22.6_D 1.4158, [α]²²_D 17.0°, without partial racemization (in contrast to the oxidation of optically active CH₂:CHCH₂CHMeCO₂H with H₂CrO₄). Using Hunsdiecker’s procedure (C.A. 37, 3734⁴) I is converted into BrCH₂CHMeCO₂Me, [α]²⁴_D 13.8°, which on hydrolysis with HBr in glacial AcOH gives BrCH₂CHMeCO₂H, [α]²⁷_D 10.1° (c 14.4, CHCl₃).

Acta Chemica Scandinavica published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is C4H3Cl2N3, Name: 3-Bromo-2-methylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Larsson, Erik published the artcileSome S-containing β-substituted derivatives of isobutyric acid, Name: 3-Bromo-2-methylpropanoic acid, the publication is Chalmers Tekniska Hoegskolas Handlingar (1944), 3-17, database is CAplus.

The preparation is described of β-alkyl, β-aryl, and β-arylalkyl sulfide derivatives, RSCH₂CHMeCO₂H (I), and of the corresponding sulfone carboxylic acids, RSO₂CH₂CHMeCO₂H (II). The synthesis of BrCH₂CHMeCO₂H (III) was improved by interacting HBr with CH₂: CMeCO₂H (IV) in CHCl₃. HSCH₂CHMeCO₂H (V) was prepared from (1) IV via MeCOSCH₂CHMeCO₂H, (2) III and NaHS, or (3) fission of EtOCS₂CH₂CHMeCO₂H prepared from EtOCS₂K and III. The Me derivative of V was prepared in aqueous solution by reaction of the di-Na salt of V with Me₂SO₄ or KMeSO₄; the Et, Pr, PhCH₂, and PhCH₂CH₂ derivatives from their halides and the di-Na salt of V in aqueous alc. solution The Ph derivative was prepared in aqueous solution from PhSNa and the Na salt of III. All of the sulfide acids (I) prepared consumed 4 equivalents of Br per mol. on oxidation in HCl solution, indicating conversion to the sulfone carboxylic acids (II). The latter were prepared by Br or KMnO₄ oxidation. The following phys. properties are given for I (R given): b.p./mm., d₄²⁰, n_D²⁰, n_F²⁰-n_C²⁰, MR_D(found) and mol. volume at 20°: Me 129-30°/12, 1.1086, 1.4815, 0.0112, 34.48, 121.1; Et 140-1°/12, 1.0684, 1.4780, 0.0110, 39.27, 138.7; Pr 138-9°/6, 1.0405, 1.4761, 0.0107, 43.97, 155.9; and PhCH₂CH₂ 190-5°/6, 1.1207, 1.5450, 0.0159, 63.28, 200.1. The I where R is iso-Pr b₈ 135-7°, m. 31°; Ph m. 45°; PhCH₂ m. 43°. The m.ps. of the following II are: Me 134°, Et 82°, Pr 75-6°, iso-Pr 109°, Ph 113°, PhCH₂ 154°, and PhCH₂CH₂ 93°. The PhCH₂ derivative of V was oxidized by K₂S₂O₈ or H₂O₂ to the sulfoxide (m. 110-11°) but the 2 theoretically possible forms of PhCH₂SOCH₂CHMeCO₂H could not be isolated. Oxidation of V with Br gave the sulfone acid. Compounds like II apparently ionize thus in alk. solution: RSO₂CH₂CHMeCO₂^– + OH^– = RSO₂^– + CH₂:CMe-CO₂^– + H₂O.

Chalmers Tekniska Hoegskolas Handlingar published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is C4H7BrO2, Name: 3-Bromo-2-methylpropanoic acid.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Mellander, Alfred published the artcileStereoisomers of α-alkylmercapto- and α-alkylsulfonepropionic acids, Product Details of C4H7BrO2, the publication is Arkiv. Kemi, Mineral. Geol. (1937), 12A(No. 16), 32 pp., database is CAplus.

The dl-form of α-propylmercaptopropionic acid, MeCH (SPr) CO₂H, was prepared by the addition of PrI (185 g.) to 106 g. α-thiolactic acid, 143 g. Na₂CO₃.10H₂O in 150 cc. H₂O and 41 g. caustic soda in 130 cc. H₂O. The α-iso-Pr derivative was similarly prepared Data are given for the following alkyl-mercapto derivatives (m. and b. ps. corrected): Me, m. 17.3°, b₉ 106.5°, d₄²⁰ 1.1464, n_D²⁰ 1.4843, M_D (mol. refraction by Lorenz-Lorentz’s formula) 29.99, k₂₅ (affinity constant by conductivity measurement) 1.73 × 10^-4; Et, b₉ 115.5°, d₄²⁰ 1.1087, n_D²⁰ 1.4798, M_D 34.35, k₂₅ 1.60 × 10^-4; Pr, b₈ 128.5°, d₄²⁰ 1.0595, n_D²⁰ 1.4765, M_D 39.47, k₂₆ 1.53 × 10^-3; isd-Pr, b₉ 121.4°, m. 14.6°, d₄²⁰ 1.0482, n_D²⁰ 1.4724, M_D 39.61, k₂₅ 1.67 × 10^-4. The corresponding sulfones, CH₃CH(SO₂R)CO₂H, were prepared by oxidation of the sulfides with KMnO₄ in alk. solution Their data follow: Me, m. 96.6°, k₂₅ 3.6 × 10^-3; Et, m. 62.6°, k₂₅ 3.25 × 10^-3; Pr, m. 59.5°; k₂₅ 3.11 × 10^-3; iso-Pr, m. 105.0°; k₂₅ 3.01 × 10^-3. Addition of Br to the sulfones gave the corresponding α-bromo-α-alkylsulfonepropionic acids as follows: Me, m. 173° (decomposition); Et, m. 96.5°; Pr, m. 125.4°; iso-Pr, m. 64.3°. Reduction of the Br derivatives with N₂H₄ gave the corresponding unsubstituted α-alkyl-sulfonepropionic acids. Resolution of dl-α-MeCH(SEt)CO₂H by crystallization of the brucine salt gave the l-form, [α]_D -111.8°, [α]_Hg -132.6°. Crystallization of the quinidine salt, m. 66-7°, from the mother liquor gave the d-form, [α]_D 111.8°, [α]_Hg 132.6°. The quinine salt of the l-Pr acid, m. 92.5-94°; the l-acid [α]_D -106.0°, [α]_Hg -126.0°. The d-acid was not isolated. d-Iso-Pr acid, [α]_D 113.7°, [α]_Hg 135.4°, was obtained by crystallization of the brucine salt, m. 76-77.5°. l-Acid, [α]_D -113.8°, [α]_Hg -135.5°, was prepared through the quinine salt, m. 132.2-4.4°. The above values of [α] were obtained by graphic interpolation of [α] values for a series of aqueous solutions of concentrations varying around 1%. The sp. rotation in aqueous solutions decreases on dilution, indicating that the undissociated acid has greater rotatory power than the ion. Distillation of the active form of the acids results in racemization. The active forms of the α-alkylsulfonepropionic acids were prepared by oxidation of the corresponding active sulfides, using KMnO₄ and phosphate buffer (p_H 6.98). The pure active forms could not be prepared by resolution of the dl-sulfones. The interpolated values of [α] for the sulfones are: l-Me [α]_D -24.5°, [α]_Hg -29.6°; d-Me [α]_D 24.5°, [α]_Hg 29.7°; l-Et [α]_D -32.7°, [α]_Hg -39.2°; d-Et [α]_D 32.6°, [α]_Hg 39.2°; l-Pr [α]_D -33.6°, [α]_Hg -40.6°; l-iso-Pr [α]_D -36.5°, [α]_Hg -44.2°; d-iso-Pr [α]_D 36.5°, [α]_Hg 44.2°.

Arkiv. Kemi, Mineral. Geol. published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is C4H7BrO2, Product Details of C4H7BrO2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Salman, Abbas Abdulameer published the artcileHybrid emulsifier systems: Alkyl imidazolium lactoside surfactants derived from natural resources, Category: bromides-buliding-blocks, the publication is Carbohydrate Research (2022), 108634, database is CAplus and MEDLINE.

A new series of hybrid surfactants comprising an imidazolium as a cation and a disaccharide as a non-ion were synthesized, and their aggregation behavior was also investigated. The synthetic approach used alkylation as an easily accessible route on an imidazole to attempt an economic production followed by coupling with bromoethyl lactoside to form lacto-imidazolium salts surfactants. The coupled surfactants were obtained in almost quant. yield over several steps. The surfactant surface properties in aqueous media were investigated, including critical micelle concentration (CMC), Krafft temperature, and emulsion stability were studied. The CMC measurements of the alkyl imidazolium lactoside surfactants are significantly lower than normal imidazolium surfactants, while the emulsion investigations encourage the use of alkyl imidazolium lactoside surfactants owing to stabilized assemble behavior as good as APGs.

Carbohydrate Research published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Category: bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Liu, Yantao published the artcileMerging Gold/Copper Catalysis and Copper/Photoredox Catalysis: An Approach to Alkyl Oxazoles from N-Propargylamides, COA of Formula: C4H6BrFO2, the publication is Journal of Organic Chemistry (2021), 86(24), 18247-18256, database is CAplus and MEDLINE.

Here, a mild and highly efficient approach to alkyl oxazoles I [R = Ph, 4-MeC₆H₄, 3-MeC₆H₄, etc.; R¹ = C₄F₉, C₆F₁₃, CCl₃, etc.] through merging gold/copper catalysis and copper/photoredox catalyzed reaction of N-propargylamides with alkyl halides was reported. Various alkyl oxazoles were synthesized in good to excellent yields with wide functional-group compatibility under blue-light irradiation Significantly, a copper catalyst played a dual role in this transformation: as a powerful cocatalyst to accelerate protodeauration of vinyl gold intermediates and improve photoredox catalysis.

Journal of Organic Chemistry published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C4H6BrFO2, COA of Formula: C4H6BrFO2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Yuan, Chunchen published the artcileRuthenium(II)-enabled para-selective C-H difluoromethylation of anilides and their derivatives, HPLC of Formula: 401-55-8, the publication is Nature Communications (2018), 9(1), 1-10, database is CAplus and MEDLINE.

Here the development of a ruthenium-enabled para-selective C-H difluoromethylation of anilides, indolines, and tetrahydroquinolines is described. This reaction tolerates various substituted arenes, affording para-difluoromethylation products in moderate to good yields. Results of a preliminary study of the mechanism indicate that chelation-assisted cycloruthenation might play a role in the selective activation of para-CAr-H bonds. Furthermore, this method provides a direct approach for the synthesis of fluorinated drug derivatives, which has important application for drug discovery and development.

Nature Communications published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C11H8F2, HPLC of Formula: 401-55-8.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary