Tag: M.W=250-300

Karlstroem, Sofia published the artcileSubstituted 7-Amino-5-thio-thiazolo[4,5-d]pyrimidines as Potent and Selective Antagonists of the Fractalkine Receptor (CX₃CR1), HPLC of Formula: 76283-09-5, the publication is Journal of Medicinal Chemistry (2013), 56(8), 3177-3190, database is CAplus and MEDLINE.

The authors have developed two parallel series, A and B, of CX₃CR1 antagonists for the treatment of multiple sclerosis. By modifying the substituents on the 7-amino-5-thio-thiazolo[4,5-d]pyrimidine core structure, they were able to achieve compounds with high selectivity for CX₃CR1 over the closely related CXCR2 receptor. The structure-activity relationships showed that a leucinol moiety attached to the core-structure in the 7-position together with α-Me branched benzyl derivatives in the 5-position displayed promising affinity, and selectivity as well as physicochem. properties, as exemplified by compounds I and II. They show the preparation of the first potent and selective orally available CX₃CR1 antagonists.

Journal of Medicinal Chemistry published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, HPLC of Formula: 76283-09-5.

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

Yoakim, Christiane published the artcileβ-Lactam Derivatives as Inhibitors of Human Cytomegalovirus Protease, COA of Formula: C8H6BrF3S, the publication is Journal of Medicinal Chemistry (1998), 41(15), 2882-2891, database is CAplus and MEDLINE.

The development of novel monobactam inhibitors of HCMV protease incorporating a carbon side chain at C-4 and a urea function at N-1 is described. Substitution with small groups at the C-3 position of the β-lactam ring gave an increase in enzymic activity and in stability; however, a lack of selectivity against other serine proteases was noted. The use of both tri- and tetrasubstituted urea functionalities gave effective inhibitors of HCMV protease. Benzyl substitution of the urea moiety was beneficial, especially when strong electron-withdrawing groups where attached at the para position. Modest antiviral activity was found in a plaque reduction assay.

Journal of Medicinal Chemistry published new progress about 21101-63-3. 21101-63-3 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,sulfides,Benzyl bromide,Benzene, name is (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, and the molecular formula is C9H8BNO2, COA of Formula: C8H6BrF3S.

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

Turunen, Lotta published the artcileHalogen Bonds of Iodonium Ions: A World Dissimilar to Silver Coordination, Synthetic Route of 52358-73-3, the publication is Bulletin of the Chemical Society of Japan (2021), 94(1), 191-196, database is CAplus.

A distinct difference between the three-center halogen bond and the analogous three-center coordinative bond of silver is demonstrated by computational, X-ray crystallog. and solution NMR spectroscopic investigations of their complexes with a bidentate Lewis base. Iodine(I) preferentially forms an entropically favored monomeric complex, whereas silver(I) forms enthalpically favored dimeric complexes. Counterion coordination considerably influences the structure of the silver complexes in the solution and solid state, whereas it does not have notable effect on the analogous halogen bond.

Bulletin of the Chemical Society of Japan published new progress about 52358-73-3. 52358-73-3 belongs to bromides-buliding-blocks, auxiliary class Bromide,Naphthalene, name is 1,3-Dibromonaphthalene, and the molecular formula is C6H20Cl2N4, Synthetic Route of 52358-73-3.

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

Garlock, Edward A. Jr. published the artcileAnthracene series. I. Methyl ketones and carbinolamines derived from 1,2,3,4-tetrahydroanthracene, HPLC of Formula: 52358-73-3, the publication is Journal of the American Chemical Society (1945), 2255-9, database is CAplus and MEDLINE.

Anthracene (I) (89 g.), 5 g. Cu chromite, and 300 cc. decalin, shaken with H at 2300 lb. and 250° for 24 min., give 43% of the 1,2,3,4-tetrahydro derivative (II); reduction at 1500 lb. and 130° gives 25% of II. Reduction of I at 2300 lb. and 150° for 5 min. gives 95% of the 9,10-dihydro derivative AcCl (20.5 cc.) and 60 g. AlCl₃ in 190 cc. PhNO₂ at -3° to -7°, treated slowly with 45.5 g. of II in 145 cc. PhNO₂, with stirring at 5° for 20 h., the resulting oil distilled at 0.1 mm. (160-70°), and crystallized from 200 cc. ligroin, give 17.6 g. of 6-acetyl-1,2,3,4-tetrahydroanthracene (III), m. 101-2°, and, from the mother liquor, 13.5 g. of the 5-isomer (IV), n_D²⁵ 1.6333 (isolated as the semicarbazone, m. 209-11°). III yields a semicarbazone, m. 251.5-2.5°; an oxime, m. 165.5-7°; and a picrate, light yellow, m. 118-20°. III (4.4 g.) in 25 cc. AcOH, treated with 5 g. CrO₃ in 3 cc. H₂O and 22 cc. AcOH at 50°, warmed to 60° for 10 min. and allowed to stand at room temperature for 1 h., gives 2.2 g. of 6-acetyl-1,2,3,4-tetrahydro-9,10-anthraquinone, yellow, m. 169-70°. III (8.96 g.) in 260 cc. EtOH at 5°, treated dropwise with 2.1 cc. Br, gives 8 g. of the 6-(ω-bromoacetyl)derivative (V), light yellow, m. 113.5-15°. III (1.1 g.), reduced with 6.5 cc. of 3 N (iso-PrO)₃Al in iso-PrOH for 15 min., gives 0.9 g. of the 6-(1-hydroxyethyl) derivative, m. 87.5-8.5°. III (2.2 g.), 10 g. amalgamated Zn, 20 cc. AcOH, 20 cc. concentrated HCl, and 8 cc. PhMe, refluxed 24 h. (three 6-cc. portions of concentrated HCl added during this period), give 1.9 g. of 6-ethyl-1,2,3,4-tetrahydroanthracene, m. 38-9.5° (picrate, bright red, m. 100-1°, very unstable). III (3.3 g.), refluxed with alk. NaOCl for 2 h., gives 2.8 g. of 1,2,3,4-tetrahydro-6-anthracenecarboxylic acid, m. 264-6°; Et ester (VI), m. 113°. Dehydrogenation of III gives 2-acetylanthracene and of VI gives Et 2-anthroate. V (6.06 g.) in 50 cc. absolute ether, treated with 6.38 g. Am₂NH, shaken for 3 h., and reduced with 30 cc. 3 N (iso-PrO)₃Al in iso-PrOH, gives 3.5 g. of 6-(2-diamylamino-1-hydroxyethyl)-1,2,3,4-tetrahydroanthracene-HCl, m. 114.5-16°; the diheptylamino homolog m. 114.5-16.5°; the dinonylamino homolog m. 112-16°. IV forms an oxime, m. 120.5-2.5°, and a picrate, light yellow, m. 115-16°. Oxidation of IV with CrO₃ in AcOH gives 5-acetyl-1,2,3,4-tetrahydro-9,10-anthraquinone, light yellow, m. 122-4°. Reduction of IV with (iso-PrO)₃Al in iso-PrOH gives 5-(1-hydroxyethyl)-1,2,3,4-tetrahydroanthracene, m. 73.5-6.5°. Oxidation of IV with NaOCl gives 1,2,3,4-tetrahydro-5-anthracenecarboxylic acid, m. 190-6°; Et ester, m. 64-70°. Dehydrogenation of IV gives 1-acetylanthracene. In the reaction of I and AcCl in C₂H₂Cl₄, the formation of III is almost entirely suppressed and the oily ketone (IV) is formed in approx. the same yield as in the PhNO₂ experiment

Journal of the American Chemical Society published new progress about 52358-73-3. 52358-73-3 belongs to bromides-buliding-blocks, auxiliary class Bromide,Naphthalene, name is 1,3-Dibromonaphthalene, and the molecular formula is C10H6Br2, HPLC of Formula: 52358-73-3.

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

Rakowitz, Dietmar published the artcileOn the synthesis of bioisosteres of O-benzothiazolyl-oxybenzoic acids and evaluation as aldose reductase inhibitors, Formula: C7H5Br2F, the publication is Archiv der Pharmazie (Weinheim, Germany) (2005), 338(9), 419-426, database is CAplus and MEDLINE.

A series of compounds characterized by bioisosteric replacement of pharmacophores were prepd, e.g., I (R = CH(=NOH) or NO₂) and tested as aldose reductase inhibitors (ARIs). On the one hand, the acidic function was formally replaced by an oxime or a nitro group and on the other hand the lipophilic substituent was modified. The results of the biol. evaluation of these derivatives permitted to gain insight into structural features critical for the aldose reductase inhibition.

Archiv der Pharmazie (Weinheim, Germany) published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Formula: C7H5Br2F.

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

Porres, Laurent published the artcileEnhanced two-photon absorption with novel octupolar propeller-shaped fluorophores derived from triphenylamine, HPLC of Formula: 21101-63-3, the publication is Organic Letters (2004), 6(1), 47-50, database is CAplus and MEDLINE.

Novel octupolar fluorophores derived from the sym. functionalization of a triphenylamine core with strong acceptor peripheral groups via phenylene-ethynylene linkers have been synthesized and shown to exhibit high fluorescence quantum yields, very large two-photon-absorption cross-sections in the red-NIR region, and suitable photostability.

Organic Letters published new progress about 21101-63-3. 21101-63-3 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,sulfides,Benzyl bromide,Benzene, name is (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, and the molecular formula is C8H6BrF3S, HPLC of Formula: 21101-63-3.

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

Miller, John C. published the artcileHeavy atom effects on the triplet lifetimes of naphthalene and phenanthrene, Synthetic Route of 52358-73-3, the publication is Journal of the American Chemical Society (1977), 99(25), 8175-9, database is CAplus.

Heavy-atom effects on triplet decay rates are reported for the 8 monohalonaphthalenes and for 11 monohalophenanthrenes. The decrease in the lifetime with substitution varies with the square of the at. spin-orbit coupling factor for the attached halogen. The position dependence is qual. related to the unpaired spin-d. distribution in the mol. Investigation of the lifetimes of 13 polyhalogenated naphthalenes and phenanthrenes indicate both pos. and neg. deviations from an additive model for heavy-atom effects. Substituent-induced shifts of the O-O band of the phosphorescence spectra are also tabulated.

Journal of the American Chemical Society published new progress about 52358-73-3. 52358-73-3 belongs to bromides-buliding-blocks, auxiliary class Bromide,Naphthalene, name is 1,3-Dibromonaphthalene, and the molecular formula is C10H6Br2, Synthetic Route of 52358-73-3.

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

Poslusney, Michael S. published the artcileSpirocyclic replacements for the isatin in the highly selective, muscarinic M₁ PAM ML137: The continued optimization of an MLPCN probe molecule, Category: bromides-buliding-blocks, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(6), 1860-1864, database is CAplus and MEDLINE.

This Letter describes the further optimization of an MLPCN probe mol. (ML137) through the introduction of 5- and 6-membered spirocycles in place of the isatin ketone. Interestingly divergent structure-activity relationships, when compared to earlier M₁ PAMs, are presented. These novel spirocycles, e.g. I, possess improved efficacy relative to ML137, while also maintaining high selectivity for the human and rat muscarinic M₁ receptor subtype.

Bioorganic & Medicinal Chemistry Letters published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Category: bromides-buliding-blocks.

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

Eckstein, Brian J. published the artcileButa-1,3-diyne-Based π-Conjugated Polymers for Organic Transistors and Solar Cells, Application In Synthesis of 303734-52-3, the publication is Macromolecules (Washington, DC, United States) (2017), 50(4), 1430-1441, database is CAplus.

We report the synthesis and characterization of new alkyl-substituted 1,4-di(thiophen-2-yl)buta-1,3-diyne (R-DTB) donor building blocks, based on the -CC-CC- conjugative pathway, and their incorporation with thienyl-diketopyrrolopyrrole (R’-TDPP) acceptor units into π-conjugated PTDPP-DTB polymers (P1-P4). The solubility of the new polymers strongly depends on the DTB and DPP solubilizing (R and R’, resp.) substituents. Thus, solution processable and high mol. weight PDPP-DTB polymers are achieved for P3 (R = n-C₁₂H₂₅, R’ = 2-butyloctyl) and P4 (R = 2-ethylhexyl, R’ = 2-butyloctyl). Systematic studies of P3 and P4 physicochem. properties are carried using optical spectroscopy, cyclic voltammetry, and thermal anal., revealing characteristic features of the dialkynyl motif. For the first time, optoelectronic devices (OFETs, OPVs) are fabricated with 1,3-butadiyne containing organic semiconductors. OFET hole mobilities and record OPV power conversion efficiencies for acetylenic organic materials approach 0.1 cm²/(V s) and 4% resp., which can be understood from detailed thin-film morphol. and microstructural characterization using AFM, TEM, x-ray diffraction, and GIWAXS methodologies. Importantly, DTB-based polymers (P3 and P4) exhibit, in addition to stabilization of frontier MOs and to -CC-CC- relief of steric torsions, discrete morphol. pliability through thermal annealing and processing additives. The advantageous materials properties and preliminary device performance reported here demonstrate the promise of 1,3-butadiyne-based semiconducting polymers.

Macromolecules (Washington, DC, United States) published new progress about 303734-52-3. 303734-52-3 belongs to bromides-buliding-blocks, auxiliary class Thiophene,Bromide, name is 2-Bromo-3-(2-ethylhexyl)thiophene, and the molecular formula is C12H19BrS, Application In Synthesis of 303734-52-3.

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

Kong, Haiyan published the artcileNovel 1-(prop-2-yn-1-ylamino)-2,3-dihydro-1H-indene-4-thiol derivatives as potent selective human monoamine oxidase B inhibitors: Design, SAR development, and biological evaluation, COA of Formula: C9H8BrF3, the publication is Bioorganic & Medicinal Chemistry Letters (2021), 128051, database is CAplus and MEDLINE.

Successes have been achieved in developing human monoamine oxidase B (hMAO-B) inhibitors as anti-Parkinson’s disease (PD) drugs. However, low efficiency and unwanted side effects of the marketed hMAO-B inhibitors hamper their medical applications, therefore, novel potent selective hMAO-B inhibitors are still of great interest. Herein we report 1-(prop-2-yn-1-ylamino)-2,3-dihydro-1H-indene-4-thiol derivatives as hMAO-B inhibitors, which were designed by employing a fragment-based drug design strategy to link rasagiline to hydrophobic fragments. Among the synthesized 31 compounds, I and II demonstrated very encouraging hMAO-B inhibitory activities and selectivity over hMAO-A, better than rasagiline and safinamide. In vitro studies indicated that K8 and K24 are nontoxic to nervous tissue cells and they have considerable effects against ROS formation and potential neuroprotective activity. Further mice behavioral tests demonstrated these two compounds have good therapeutic effects on MPTP-induced PD model mice. All these experiment results suggest that compounds K8 and K24 can be promising candidates for further research for treatment of PD.

Bioorganic & Medicinal Chemistry Letters published new progress about 1997-80-4. 1997-80-4 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Benzene, name is 1-(2-Bromoethyl)-3-(trifluoromethyl)benzene, and the molecular formula is C9H8BrF3, COA of Formula: C9H8BrF3.

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