Tag: M.W=200-250

Verma, Naimish K. published the artcileRegioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazole Derivatives from α,β-Unsaturated Carbonyls, Computed Properties of 143-15-7, the publication is European Journal of Organic Chemistry (2022), 2022(28), e202200317, database is CAplus.

The copper-catalyzed oxidative azide-olefin cycloaddition (OAOC) reaction of differently substituted α,β-unsaturated carbonyls with azides provided an efficient method for preparing biol. active 1,4,5-trisubstituted 1,2,3-triazoles. In this study, the cycloaddition reaction was found to be a simple and powerful method for constructing diverse mono- and bis-(1,4,5-trisubstituted 1,2,3-triazole) functionalized heterocyclic compounds in moderate to high yields with great regioselectivity. The XRD-anal. data of one of the bis-triazole derivatives supported the regioselectivity as well as the conformity of the method in the construction of the triazole nucleus. The preliminary antifungal profile against C. albicans was observed with cinnamaldehyde-based triazole derivatives demonstrating promising results.

European Journal of Organic Chemistry published new progress about 143-15-7. 143-15-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromododecane, and the molecular formula is C23H43NP2, Computed Properties of 143-15-7.

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

Nazarov, I. N. published the artcileStereochemistry of addition reactions at a triple bond. III. Stereochemistry of bromination of propargyl alcohols, HPLC of Formula: 594-81-0, the publication is Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1960), 887-95, database is CAplus.

cf. CA 52, 3660g, 19925f. Photochem. bromination of HCCCH₂OH (I) yielded trans-dibromide, while the tertiary acetylenic alcs. and acetates yielded mainly cis-dibromides. I and the calculated amount of Br in CCl₄ added at 25° under ultraviolet light gave 74% 2,3-dibromo-2-propen-1-ol, b₁ 55-6°, m. 28-30°, whose trans structure was confirmed by infrared spectrum (shown). Bromination of dimethylethynylcarbinol in hexane under ultraviolet light gave 2,3-dibromo-2,3-dimethylbutane, m. 173-5°, and mainly a stereoisomeric mixture of dibromovinyldimethylcarbinols, b₆ 76-80°, n_D²⁰ 1.5422, containing not over 8% trans isomer. Similar bromination of HCCCMe₂OAc gave a little 2,3-dibromo-2,3-dimethylbutane, m. 172-5°, and 77% stereoisomers of AcOCMe₂CBr:CHBr, b₂ 71-4.5°, n_D^21.5 1.5184, containing not over 11% trans isomer. Similar bromination in AcOH gave the above mixture, b₁₀ 80-103°, a fraction, b₁₀ 103-8°, n_D²⁰ 1.4909 [which with semicarbazide gave bromoacetyldimethylcarbinyl acetate semicarbazone, m. 102-5° (CA 36, 745⁸)], and a polybromoketone, b₃ 91-106°, 1.5278. The mother liquors yielded with semicarbazide bromoacetyldimethylcarbinylsemicarbazide, m. 125-6°. cis-Dibromovinyldimethylcarbinyl acetate with MeONa-MeOH (loc. cit.) in the cold gave cis-dibromoethylene, containing not over 5% trans isomer, and mostly dimethylbromoethynylcarbinol, b₁₇ 68-70°; p-nitrobenzoate m. 88.5-9.5° (Straus, et al., CA 25, 71). The residues yielded some Me₂C:CHCO₂H. trans-CHBr: CBrCMe₂OH with Ac₂OH₂SO₄ in the cold gave mainly trans-3,4-dibromoisoprene and trans-CHBr:CBrCMe₂OAc, b₁ 68-9°, 1.513-6, which with MeONa-MeOH gave trans-dibromoethylene and trans-CHBr:CBrCMe₂OH. The latter and powd. KOH in Et₂O in 2 hrs. at 35° gave 22% dibromoethylene, containing not over 16% cis form, along with unreacted material and some (CCMe₂OH)₂. Bromination of 1-ethynylcyclohexyl acetate in hexane under ultraviolet light gave 82% cis-1-(dibromovinyl)cyclohexyl acetate, b_2.5 116-18°, n_D¹⁹ 1.5321. Similar bromination in AcOH at room temperature gave 60% 1-acetoxy-1-(dibromoacetyl)cyclohexanone, m. 51.5-2°, and mixed stereoisomers of 1-(dibromovinyl)cyclohexyl acetates, b₁ 101-4°, containing not over 13% cis-isomer. Keeping cis-1-(dibromovinyl)cyclohexyl acetate with alc. KOH 3 days gave 69% 1-bromoethynylcyclohexanol, m. 54.5-6°, and 13.5% cyclohexylideneacetic acid; S-benzylthiuronium salt m.162-3°. trans-1-(Dibromovinyl)cyclohexanol with Ac₂OH₃PO₄ gave the corresponding acetate, b_1.2 105.5-6°, n_D²⁰ 1.5388. Ultraviolet irradiation of trans-dibromovinyldimethylcarbinol in hexane in the presence of a trace of Br 4 hrs. gave 81% cis-isomer; longer irradiation failed to increase this conversion. The trans-isomer kept 2 months in the dark yielded 69% cis-isomer. Irradiation of trans-(dibromovinyl)dimethylcarbinyl acetate gave also a mixture of cis-trans isomers containing 78% cis-form. The liquid trans-1-(dibromovinyl)cyclohexanol, illuminated in hexane solution, solidified and gave some 79% cis-isomer; keeping the trans-isomer 6 months in the cold gave 62% cis-isomer, m. 66-70°. The estimation of cis-trans isomers was done with the aid of infrared spectra, which were shown.

Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C6H12Br2, HPLC of Formula: 594-81-0.

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

Storch, Jan published the artcileIntramolecular cascade hydroarylation/cycloisomerization strategy for the synthesis of polycyclic aromatic and heteroaromatic systems, Safety of (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is European Journal of Organic Chemistry (2013), 2013(2), 260-263, database is CAplus.

A new PtCl₂/PtCl₄-catalyzed hydroarylation/cycloisomerization cascade reaction leading to the formation of two aromatic or heteroaromatic rings in one step is reported. The strategy developed is exemplified by the synthesis of the 5,6-dihydrobenzo[c]phenanthrene and 6H-naphtho[2,1-c]chromene skeletons. Attempts to prepare [8]helicene-like mols. are also discussed.

European Journal of Organic Chemistry published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C15H14O3, Safety of (4-Bromobut-1-yn-1-yl)trimethylsilane.

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

Zhang, Dapeng published the artcileThe Unexpected Importance of the Primary Structure of the Hydrophobic Part of One-Component Ionizable Amphiphilic Janus Dendrimers in Targeted mRNA Delivery Activity, Safety of 1-Bromododecane, the publication is Journal of the American Chemical Society (2022), 144(11), 4746-4753, database is CAplus and MEDLINE.

Viral and synthetic vectors for delivery of nucleic acids impacted genetic nanomedicine by aiding the rapid development of the extraordinarily efficient Covid-19 vaccines. Access to targeted delivery of nucleic acids is expected to expand the field of nanomedicine beyond most expectations. Both viral and synthetic vectors have advantages and disadvantages. The major advantage of the synthetic vectors is their unlimited synthetic capability. The four-component lipid nanoparticles (LNPs) are the leading nonviral vector for mRNA used by Pfizer and Moderna in Covid-19 vaccines. Their synthetic capacity inspired us to develop a one-component multifunctional sequence-defined ionizable amphiphilic Janus dendrimer (IAJD) delivery system for mRNA. The first experiments on IAJDs provided, through a rational-library design combined with orthogonal-modular accelerated synthesis and sequence control in their hydrophilic part, some of the most active synthetic vectors for the delivery of mRNA to lung. The second experiments employed a similar strategy, generating, by a less complex hydrophilic structure, a library of IAJDs targeting spleen, liver, and lung. Here, we report preliminary studies designing the hydrophobic region of IAJDs by using dissimilar alkyl lengths and demonstrate the unexpectedly important role of the primary structure of the hydrophobic part of IAJDs by increasing up to 90.2-fold the activity of targeted delivery of mRNA to spleen, lymph nodes, liver, and lung. The principles of the design strategy reported here and in previous publications indicate that IAJDs could have a profound impact on the future of genetic nanomedicine.

Journal of the American Chemical Society published new progress about 143-15-7. 143-15-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromododecane, and the molecular formula is C7H7ClN2S, Safety of 1-Bromododecane.

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

Gopalsamy, Ariamala published the artcilePF-07059013: A Noncovalent Modulator of Hemoglobin for Treatment of Sickle Cell Disease, Name: 2-Amino-5-bromo-3-fluorobenzaldehyde, the publication is Journal of Medicinal Chemistry (2021), 64(1), 326-342, database is CAplus and MEDLINE.

Sickle cell disease (SCD) is a genetic disorder caused by a single point mutation (β6 Glu → Val) on the β-chain of adult Hb (HbA) that results in sickled Hb (HbS). In the deoxygenated state, polymerization of HbS leads to sickling of red blood cells (RBC). Several downstream consequences of polymerization and RBC sickling include vaso-occlusion, hemolytic anemia, and stroke. We report the design of a noncovalent modulator of HbS, clin. candidate PF-07059013 (23). The seminal hit mol. was discovered by virtual screening and confirmed through a series of biochem. and biophys. studies. After a significant optimization effort, we arrived at 23, a compound that specifically binds to Hb with nanomolar affinity and displays strong partitioning into RBCs. In a 2-wk multiple dose study using Townes SCD mice, 23 showed a 37.8% (±9.0%) reduction in sickling compared to vehicle treated mice. 23 (PF-07059013) has advanced to phase 1 clin. trials.

Journal of Medicinal Chemistry published new progress about 906811-51-6. 906811-51-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Amine,Benzene,Aldehyde, name is 2-Amino-5-bromo-3-fluorobenzaldehyde, and the molecular formula is C7H5BrFNO, Name: 2-Amino-5-bromo-3-fluorobenzaldehyde.

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

Alonso, Diego A. published the artcile3,5-Bis(trifluoromethyl)phenyl sulfones in the synthesis of 3,5-disubstituted cyclopent-2-enones, Category: bromides-buliding-blocks, the publication is ARKIVOC (Gainesville, FL, United States) (2007), 243-262, database is CAplus.

3,5-Bis(trifluoromethyl)phenyl sulfones {BTFP sulfones; 3,5-(CF₃)₂C₆H₃S(O)₂CH₂R; R = Ph, C₆H₄NO₂-4, CO₂ⁱPr, CN, P(O)(OEt)₂; 1a–e}, easily synthesized from 3,5-bis(trifluoromethyl)benzenethiol, react under PTC with (Z)-1,4-dichloro-2-butene to afford the cyclopentenyl sulfones {3; 4-(3,5-(CF₃)₂C₆H₃S(O)₂)-4-Rcyclopentene}, which suffer further diastereoselective alkene epoxidation with MCPBA giving BTFP sulfonyl cyclopentene oxides with the dominant isomer having the sulfonyl away from the oxygen bridge in good yields. These epoxides are convenient precursors of 3,5-disubstituted cyclopent-2-enones (e.g. 5-bromo-3-phenyl-2-cyclopenten-1-one), which result from epoxide ring-opening with different nucleophiles and final successive oxidation-BTFP sulfinate elimination.

ARKIVOC (Gainesville, FL, United States) published new progress about 66197-72-6. 66197-72-6 belongs to bromides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyl (bromomethyl)phosphonate, and the molecular formula is C5H12BrO3P, Category: bromides-buliding-blocks.

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

Boardman, Larry D. published the artcileMetal promoted cyclization. 5. Mechanistic duality in cycloalkylation of alkenylmetal derivatives, Safety of (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Journal of the American Chemical Society (1984), 106(20), 6105-7, database is CAplus.

Cycloalkylation of ω-halo-1-alkenylmetals can proceed by either a σ- or a π-type cyclization process. The σ-process, observed with alkenyllithium derivatives, is applicable to the formation of four- through seven-membered cycloalkenes. It does not require the second metal, e.g., Si, but requires the cis relationship between Li and the cyclizing moiety, and is regiospecific. The required (Z)-1-iodo-ω-bromo-1-alkenes may conveniently be prepared via carbometalation of alkynes with alkenylmetals followed by iodinolysis, treatment with (Me₂CHCH₂)₃Al-Cl₂ZrCp₂, and brominolysis with NBS. On the other hand, the π-process, observed with 1,1-dimetallo-ω-halo-1-alkenes (I, M¹ = Al, Zn, Zr, Si; M² = Si, Zn, Al, Zr; R = H, alkyl; X = halo) has been applied to the synthesis of three-, four-, and six-membered cycloalkenes, the relative ease of cyclization being 3, 4 ≫ 5 < 6. This process seems to require two metals, but the alkene geometry is unimportant. It can be regioselective but nonregiospecific.

Journal of the American Chemical Society published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C7H13BrSi, Safety of (4-Bromobut-1-yn-1-yl)trimethylsilane.

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

Stoelevik, Reidar published the artcileConformational analysis of 1,2-dihalotetramethylethanes and 1,2-dihalotetramethyldisilanes by molecular mechanics calculations, Computed Properties of 594-81-0, the publication is Journal of Molecular Structure (1989), 131-5, database is CAplus.

By using nonbonding atom···atom interaction potentials derived from gas-phase data on related haloalkanes, torsional potentials of the title mols. are calculated These mols. have stable anti and gauche conformations. In all mols. the anti has a lower energy than the gauche. The rotational barrier heights corresponding to a transition from gauche to anti are 0.5-1.5 kcal mol^-1 in the disilanes and 3.5-5.5 kcal mol^-1 in the ethanes. Calculated results are compared with the gas-phase observations on the disilanes.

Journal of Molecular Structure published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C10H16O2, Computed Properties of 594-81-0.

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

Decroos, Christophe published the artcileToward Stable Electron Paramagnetic Resonance Oximetry Probes: Synthesis, Characterization, and Metabolic Evaluation of New Ester Derivatives of a Tris-(para-carboxyltetrathiaaryl)methyl (TAM) Radical, Computed Properties of 55788-44-8, the publication is Chemical Research in Toxicology (2013), 26(10), 1561-1569, database is CAplus and MEDLINE.

Tris-(p-carboxyltetrathiaaryl)-Me (TAM) radicals, such as 1a (“Finland” radical), are useful EPR probes for oximetry. However, they are rapidly metabolized by liver microsomes in the presence of NADPH, with the formation of diamagnetic quinone-methide metabolites resulting from an oxidative decarboxylation of one of their carboxylate substituents. In an effort to obtain TAM derivatives potentially more metabolically stable in vivo, the authors synthesized four new TAM radicals in which the carboxylate substituents of 1a have been replaced with esters groups bearing various alkyl chains designed to render them water-soluble The new compounds were completely characterized by UV-visible and EPR spectroscopies, high resolution mass spectrometry (HRMS), and electrochem. Two of them were water-soluble enough to undergo detailed microsomal metabolic studies in comparison with 1a. They are stable in the presence of the esterases present in rat liver microsomes and cytosol, and, contrary to 1a, stable to oxidation in the presence of NADPH-supplemented microsomes. A careful study of their possible microsomal reduction under anaerobic or aerobic conditions showed that they were more easily reduced than 1a, in agreement with their higher reduction potentials. They were reduced into the corresponding anions not only under anaerobic conditions but also in the presence of dioxygen. These anions were much more stable than that of 1a and could be characterized by UV-visible spectroscopy, MS, and at the level of their protonated product. However, they were oxidized by O₂, giving back to the starting ester radicals and catalyzing a futile cycle of O₂ reduction Such reactions should be considered in the design of future stable EPR probes for oximetry in vivo.

Chemical Research in Toxicology published new progress about 55788-44-8. 55788-44-8 belongs to bromides-buliding-blocks, auxiliary class Bromide,Salt,Aliphatic hydrocarbon chain,Aliphatic hydrocarbon chain, name is Sodium 3-bromopropane-1-sulfonate, and the molecular formula is C3H6BrNaO3S, Computed Properties of 55788-44-8.

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

Hubbard, Robert D. published the artcilePyrazolo[3,4-d]pyrimidines as potent inhibitors of the insulin-like growth factor receptor (IGF-IR), Category: bromides-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry Letters (2007), 17(19), 5406-5409, database is CAplus and MEDLINE.

A high throughput screen of Abbott’s compound repository revealed that the pyrazolo[3,4-d]pyrimidine class of kinase inhibitors, e.g., I, possessed moderate potency for IGF-IR, a promising target for cancer chemotherapy. The synthesis and subsequent optimization of this class of compounds led to the discovery of I that possesses in vivo IGF-IR inhibitory activity.

Bioorganic & Medicinal Chemistry Letters published new progress about 53484-26-7. 53484-26-7 belongs to bromides-buliding-blocks, auxiliary class Bromide,Nitro Compound,Amine,Benzene, name is 4-Bromo-N-methyl-2-nitroaniline, and the molecular formula is C7H7BrN2O2, Category: bromides-buliding-blocks.

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