Month: December 2022

Lim, Chae Jo published the artcile4-Heteroaryl phthalazin-1(2H)-one derivatives as potent melanin concentrating hormone receptor 1 (MCH-R1) antagonists, Related Products of chlorides-buliding-blocks, the publication is Bulletin of the Korean Chemical Society (2012), 33(7), 2389-2392, database is CAplus.

The target compounds, 4-heteroaryl-2-{3-[4-(3-acetamidophenyl)piperidin-1-yl]propyl}phthalazin-1(2H)-ones, were prepared starting from 2-BrC₆H₄CO₂H in 4 steps starting via Li-halo exchange using excess BuLi, followed by acylation with appropriate heteroaroyl esters to give the corresponding 2-heteroaroylbenzoates. The key 4-heteroarylphthalazin-1(2H)-one intermediates were then generated by condensation with N₂H₄. Subsequent N-alkylation with Cl(CH₂)₃I using NaH base afforded 2-(3-chloropropyl)4-heteroarylphthalazin-1 (2H)-ones, which were transformed to the target compounds through coupling with N-[3-(4-piperidinyl)phenyl]acetamide in the presence of Na₂CO₃. The title compounds proved to be potent MCH-R1 antagonists. An extensive SAR study carried out with substances in this family containing C(4) pyridyl and 5-membered heteroaryl groups led to the identification of a 5-chlorothien-2-yl derivative as a highly potent MCH-R1 antagonist. This substance displayed good metabolic stability, no inhibition of CYP450 enzymes, and low hERG binding activity.

Bulletin of the Korean Chemical Society published new progress about 6313-54-8. 6313-54-8 belongs to chlorides-buliding-blocks, auxiliary class Pyridine,Chloride,Carboxylic acid, name is 2-Chloroisonicotinic acid, and the molecular formula is C6H4ClNO2, Related Products of chlorides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Arthuis, Martin published the artcilePd⁰-Catalyzed carbonylation of 1,1-dichloro-1-alkenes, a new selective access to Z-α-chloroacrylates, HPLC of Formula: 866-23-9, the publication is Chemical Communications (Cambridge, United Kingdom) (2010), 46(41), 7810-7812, database is CAplus and MEDLINE.

A novel and fully chemo- and stereoselective three component strategy leading to Z-α-chloroacrylates by a Pd⁰-catalyzed reaction of CO (1 atm) with 1,1-dichloro-1-alkenes and various alcs. is disclosed. This catalytic approach compares favorably with the Wittig type strategies as α-chloroacrylates of pure Z configuration are obtained in high yield.

Chemical Communications (Cambridge, United Kingdom) published new progress about 866-23-9. 866-23-9 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyltrichloromethylphosphonate, and the molecular formula is C5H10Cl3O3P, HPLC of Formula: 866-23-9.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Cooperstein, S. J. published the artcileThe mechanism of Janus Green B staining of mitochondria. II. Reactions and properties of Janus Green B and its derivatives, HPLC of Formula: 4569-86-2, the publication is Experimental Cell Research, Supplement (1953), 69-82, database is CAplus.

The absorption spectra are reported of Janus Green B(I) and G(II) and their derivatives, diethylsafranine, leucosafranine, and dimethylsafranine. I was readily reduced by cysteine (III) and glutathione whereas II was not significantly reduced by III. At pH 7.48 I showed 2 reduction steps upon polarographic analysis, one at a potential of -0.001 v. and the other at -0.188 v. II had only one reduction step at -0.214 v.

Experimental Cell Research, Supplement published new progress about 4569-86-2. 4569-86-2 belongs to chlorides-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Salt,Amine,Benzene, name is 3-Amino-7-(diethylamino)-5-phenylphenazin-5-ium chloride, and the molecular formula is C22H23ClN4, HPLC of Formula: 4569-86-2.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Schrittwieser, Joerg H. published the artcileBiocatalytic Cascade for the Synthesis of Enantiopure β-Azidoalcohols and β-Hydroxynitriles, HPLC of Formula: 5034-06-0, the publication is European Journal of Organic Chemistry (2009), 2293-2298, database is CAplus.

A three-step, two-enzyme, one-pot reaction sequence starting from prochiral α-chloroketones leading to enantiopure β-azidoalcs. and β-hydroxynitriles was described. Asym. bioreduction of α-chloroketones by hydrogen transfer catalyzed by an alc. dehydrogenase (ADH) established the stereogenic center in the first step to furnish enantiopure chlorohydrin intermediates. Subsequent biocatalyzed ring closure to the epoxide and nucleophilic ring opening with azide, N₃^–, or cyanide, CN^–, both catalyzed by a nonselective halohydrin dehalogenase (Hhe), proceeded with full retention of configuration to give enantiopure β-azidoalcs. and β-hydroxynitriles, resp. Both enantiomers of various optically pure β-azidoalcs. and β-hydroxynitriles were synthesized. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009).

European Journal of Organic Chemistry published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, HPLC of Formula: 5034-06-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Coutrot, Philippe published the artcileSynthesis of diethyl 1,1-dichloroalkane- and 1-chloroalkanephosphonates, Computed Properties of 866-23-9, the publication is Synthesis (1977), 615-17, database is CAplus.

RCCl2P(O)(OEt)2 (I, R = Me, Et, Pr, Bu, CH2:CHCH2, MeCH:CHCH2, MeOCH2) and RR1CClP(O)(OEt)2 (II, R = Me, Et, Pr, Bu; R1 = H, Me, Et, Bu, CH2:CHCH2, Cl(CH2)3) (11 compounds) were prepared in 42-81 and 66-89% yields resp. Thus, alkylation of (EtO)2P(O)CCl2Li with RBr in presence of PO(NMe2)3 at -80° gave I. Lithiation of I followed by alkylation with R1X (X = Br, iodo) gave II.

Synthesis published new progress about 866-23-9. 866-23-9 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is Diethyltrichloromethylphosphonate, and the molecular formula is C5H10Cl3O3P, Computed Properties of 866-23-9.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Hunziker, F. published the artcileChemistry and pharmacology of dibenzo[b,e][1,4]diazepine derivatives with basic substituents in position 10, Quality Control of 60091-87-4, the publication is Arzneimittel-Forschung (1963), 324-8, database is CAplus and MEDLINE.

A series of I derivatives was prepared according to Clemo, et al. (CA 19, 293) and Burton and Gibson (CA 19, 987) by an Ullmann-synthesis from o-bromonitrobenzenes and free anthranilic acid derivatives in presence of K₂CO₃ and catalytic amounts of Cu in a higher alcohol as solvent. The N-methylated anthranilic acids gave lower yields (50-60%) than the corresponding primary amines. The esters of I were best obtained via the acid chlorides. Thus, the following I derivatives were prepared (R¹, R², R³, and m.p. given): H, 4-Me, H, 213-15°; H, 4-Me, Et, 99-100°; Me, 4-Me, H, 140-1°; H, 4-Cl, H, 245-8°; H, 4-Cl, Et, 134-6°; Me, 4-Cl, H, 139-42°; H, 4-CF₃, H, 225-6°; H, 4-CF₃, Me, 147-8°; Me, 4-CF₃, H, 154-6°; H, 4-OMe, H, 228-30°; H, OMe, Et, 104°; Me, 4-OMe, H, 164-6°; H, 5-Cl, Me, 157-8°; H, 5-Cl, Et, 127-8°; Me, 5-Cl, H, 160°; Me, 5-Cl, Me, 92-3°; H, 5-OMe, Me, 149°; H, 5-SMe, Et, 187-8°; Me, 5-SMe, Me, 102-3°; H, 6-Cl, Me, 119-20°; H, 5′-Cl, Et, 106-7°; H, 5′-OMe, H, 235-7°; H, 4′-Cl, H, 232-5°; H, 4′-Cl, Me, 138°; H, 4′-OMe, H, 240°; Me, 4′-OMe, H, 168-72°. To a cooled solution of 5.9 g. K in 110 ml. tert-BuOH was added under stirring 12 g. MeSH. At 20°, a solution of 40.3 g. I (R¹ = R³ = Me, R² = 5-Cl) in 300 ml. HCONMe₂ was added. After 2 hrs. stirring at 80°, evaporation to dryness in vacuo, distribution between benzene and NaHCO₃ solution, evaporation of the benzene, and crystallization from Et₂O/petr. ether gave 40 g. I (R¹ = R³ = Me, R² = 5-SMe), m. 102-3°. To 135.6 g. I (R¹ = R³ = H, R² = 5-Cl) 10.3, suspended in 1.8 l. 2N aqueous NH₃ was added within 3 hrs. 266 g. Na₂S₂O₄. The mixture was heated to 80° till solution was complete. Charcoal treatment, acidification to pH 4.5 with AcOH, addition of NaCl, and work-up gave 121.3 g. II (R¹ = R³ = H, R² = 5-Cl), m. 208-5° (decomposition) (MeOH-H₂O). Similarly prepared were the II derivatives (R¹, R², R³, m.p. given): H, 4-Me, H, 213-15°; Me, 4-Me, H, 144-6°; H, 4-Cl, H, 200-5°; Me, 4-Cl, H, 155°; H, 4-CF₃, H, 214-15°; Me, 4-CF₃, H, 160°; H, 4-OMe, H, 200°; Me, 4-OMe, H, 132-4°; H, 5-Cl, Me, 117-18°; Me, 5-Cl, H, 155°; H, 5-OMe, H, 178-9°; H, 5-SMe, H, 170-2°; H, 6-Cl, Me, 135-9°; H, 5′-Cl, H, 175-7°; H, 5′-OMe, H, 182-4°; H, 4′-Cl, H, 197-8°. II (R¹ = R³ = H, R² = 5-Cl) (121.3 g.) was refluxed in 3 l. xylene 40 hrs. under continuous removal of H₂O. After distillation of the solvent and vapor distillation for removal of impurities, the residue was made alkaline with dilute NH₃, filtered, treated with charcoal, and crystallized from Me₂CO-H₂O to give 71.3 g. III (R¹ = H, R² = 7-Cl), m. 253-4°. The same compound was also obtained by refluxing of 2.5 g. II (R¹ = H, R² = 5-Cl, R³ = Me) with 0.39 g. NaNH₂ in 20 ml. dioxane, dilution with H₂O, and filtration in 83% yield. Similarly prepared were the following III derivatives (R¹, R², m.p. given): H, 2-Cl, 259-60°; H, 2-OMe, 220-1°; Me, 2-OMe, 200-12°; H, 3-Cl, 271°; H, 3-OMe, 232-3°; H, 3-Me, 267-9°; H, 6-Cl, 244-6°; Me, 7-Cl, 226-7°; H, 7-OMe, 239-40°; H, 7-SMe, 211-12°; Me, 7-SMe, 225-6°; H, 8-Cl, 231-2°; Me, 8-Cl, 214-15°; H, 8-Me, 194-5°; Me, 8-Me, 228-9°; H, 8-CF₃, 176-7°; Me, 8-CF₃, 239-40°; H, 8-OMe, 174-6°; Me, 8-OMe, 221-3°. III (R¹ = H, R² = 7-Cl) (52.5 g.) was refluxed 1 hr. with 9.2 g. NaNH₂ in 350 ml. dioxane, then 29 g. ClCH₂CH₂NMe₂ in 50 ml. benzene was added and the mixture refluxed 16 hrs. Concentration in vacuo, distribution between benzene/H₂O, extraction of the benzene with diluted HCl, alkalinization of the extract with NH₃, extraction with CHCl₃, evaporation of the solvent, and crystallization from Me₂CO/Et₂O gave 50.8 g. IV (R¹ = H, R² = 7-Cl), m. 165-6°, _ε230 32,740 (EtOH); hydrochloride m. 225-33° (EtOH-Et₂O). The same compound was obtained by refluxing 11.4 g. II (R¹ = H, R² = 5-Cl, R³ = Me) 90 min. with 1.8 g. NaNH₂ in 90 ml. dioxane, then adding 6 g. ClCH₂CH₂NMe₂ in 20 ml. benzene, and refluxing 15 hrs. (and usual work-up) in 56% yield. Similarly prepared were the following IV derivatives (R¹ R², m.p. free base, m.p. hydrochloride, L.D.₅₉ mg./kg. mouse per os given): H, H, 112-14°, -, 705; Me, H, 116-17°, 234-40°, 215; H, 2-Cl, 172-3°, -, 175; Me, 2-OMe, -, 205-10°, 900; H, 3-Cl, 159-60°, -, 305; H, 3-OMe, 141-3°, -, 150; H, 6-Cl, 122-3°, -, 260; H, 7-Cl, 165-6°, 225-33°, 330; Me, 7-Cl, -, 247-53°, 500; H, 7-OMe, 152-3°, -, 220; H, 7-SMe, 126-9°, -, 345; Me, 7-SMe, -, 205-7°, 520; H, 8-Cl, 140-5°, -, -; Me, 8-Cl, -, 240-5°, 500; H, 8-OMe, 126-7°, -, 220; H, 8-CF₃, 115-18°, -, 150; Me, 8-CF₈, -, 222-6°, 240; H, 8-Me, 137-8°, -, 127; Me, 8-Me, -, 214-17°, 100. Also prepared were the V derivatives (X, m.p., D.L.₅₀ mg./kg. mouse per os given): 2-pyrrolidinoethyl, 159-60°, 700; 2-piperidinoethyl, 187-9°, 700; 2-morpholinoethyl, 220-2°, >2500; CH₂CHMeNMe₂, 197-9°, 320; (CH₂)₃NMe₂, 137-9°, 1000. Reduction of the corresponding oxo derivatives with LiAlH₄ in tetrahydrofuran gave the VI derivatives (R¹, R², m.p., L.D.₅₀ mg./kg. mouse per os given): H, H, (maleate m. 100°), 600; Me, H, – (maleate m. 149-51°), 760; H, Cl, 87-9°, 275. IV (R¹ = H, R² = 2-Cl) (20 g.) was refluxed 24 hrs. in 200 ml. 5N HCl. Concentration in vacuo, addition of NaOH, and isolation of the resulting base gave 14.8 g. VII, b_8.97 130-8°. Acetylation with Ac₂O in pyridine gave VIII, m. 109-11°. To prove the structure, VIII was also synthesized independently. Thus, IX was acetylated to give X, m. 89-90° (Et₂O-petr. ether). X (31 g.) was alkylated with 4 g. NaNH₂ and 9.5 g. ClCH₂CH₂NMe₂ in 150 ml. dioxane to give after usual work-up 31.5 g. VIII. To test the influence of the N bridge on the pharmacol. properties, XI was prepared by refluxing 11.7 g. phenanthridone with 2.95 g. NaNH₂ in 120 ml. dioxane for 2 hrs. Addition of 7 g. ClCH₂CH₂NMe₂ in 50 ml. dioxane during 4 hrs., refluxing for 10 hrs, and normal work-up gave XI; hydrochloride m. 268-70° (MeOH-Et₂O). The XII derivatives were also prepared (X, m.p., L.D.₅₀ mg./kg. mouse per os given): S, 268-71° (hydrochloride) 870; SO₂, 113-23°, 620; O, 230-3° (hydrochloride), 500. The influence of the chem. constitution on the pharmacological activity was studied. A heterocyclic bridge in position 5 is indispensable for activity; derivatives of benzanilide and phenanthridone having basic substituents are inactive. An unsubstituted NH-group in position 5 has a more favorable effect than the Me-substituted N and is superior in activity to other hetero-bridges such as SO₂, S, and O. Compounds with substituents in position 7 show greater activity than the unsubstituted compound A carbonyl group in position 11 is essential for activity, the corresponding VI derivatives, although closely related to known antihistamines of the benzylaniline group are practically inactive in vivo. In agreement with other classes of antihistamines, the (CH₂)₂NMe₂ and (CH₂)₃NMe₂ groups are the most effective basic substituents. IV (R¹ = H, R² = 7-Cl) and the corresponding 7-SMe derivative belong to the most potent antihistaminics of today.

Arzneimittel-Forschung published new progress about 60091-87-4. 60091-87-4 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Nitro Compound,Carboxylic acid,Amine,Benzene, name is 2-((4-Chloro-2-nitrophenyl)amino)benzoic acid, and the molecular formula is C13H9ClN2O4, Quality Control of 60091-87-4.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Hovlid, Marisa L. published the artcileEncapsidated Atom-Transfer Radical Polymerization in Qβ Virus-like Nanoparticles, Safety of 2-Chlorotrityl chloride, the publication is ACS Nano (2014), 8(8), 8003-8014, database is CAplus and MEDLINE.

Virus-like particles (VLPs) are unique macromol. structures that hold great promise in biomedical and biomaterial applications. The interior of the 30 nm-diameter Qβ VLP was functionalized by a three-step process: (1) hydrolytic removal of endogenously packaged RNA, (2) covalent attachment of initiator mols. to unnatural amino acid residues located on the interior capsid surface, and (3) atom-transfer radical polymerization of tertiary amine-bearing methacrylate monomers. The resulting polymer-containing particles were moderately expanded in size; however, biotin-derivatized polymer strands were only very weakly accessible to avidin, suggesting that most of the polymer was confined within the protein shell. The polymer-containing particles were also found to exhibit phys. and chem. properties characteristic of pos. charged nanostructures, including the ability to easily enter mammalian cells and deliver functional small interfering RNA.

ACS Nano published new progress about 42074-68-0. 42074-68-0 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Benzyl chloride,Benzene, name is 2-Chlorotrityl chloride, and the molecular formula is C19H14Cl2, Safety of 2-Chlorotrityl chloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Mantell, Mark A. published the artcileS_NAr and C-H Amination of Electron Rich Arenes with Pyridine as a Nucleophile Using Photoredox Catalysis, Synthetic Route of 637-07-0, the publication is Organic Letters (2021), 23(13), 5213-5217, database is CAplus and MEDLINE.

The development of two photocatalytic methods for the pyridination of electron rich arenes was described. First, an SNAr-type reaction between aryl halides and pyridine was developed and optimized. This transformation affords selective substitution of C(sp²)-halogen over C(sp²)-OR bonds to afford arylpyridinium products under anaerobic conditions. Under complementary aerobic conditions, analogous substrates were shown to undergo oxidative C(sp²)-H pyridination.

Organic Letters published new progress about 637-07-0. 637-07-0 belongs to chlorides-buliding-blocks, auxiliary class Inhibitor,Cell Cycle,PPAR, name is Ethyl 2-(4-chlorophenoxy)-2-methylpropanoate, and the molecular formula is C12H15ClO3, Synthetic Route of 637-07-0.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Delzenne, Gerard A. published the artcilePhotosensitive polymers. I. Synthesis and properties of coumarin-modified polymers, Recommanded Product: Coumarin-6-sulfonyl chloride, the publication is Industrie Chimique Belge (1967), 32(Spec. No.), 373-8, database is CAplus.

Polymers containing intramol. cinnamic esters of the coumarin type were synthesized by treating a poly(hydroxy ether) or partially hydrolyzed poly(vinyl butyral) with 6-coumarincarbonyl chloride, 6-coumarinsulfonyl chloride, or 7-coumarinyl 3-(chlorocarbonyl)-benzenesulfonate. A coumarin-containing copolymer was obtained by copolymerization of Et acrylate and 7-(acryloyloxy)coumarin. The photodimerization of coumarin functions by formation of a cyclobutane structure was useful for imagewise insolubilization of polymers. The photosensitivity of these polymers was compared with the sensitivity of poly(vinyl cinnamate). There was a linear relationship between the light sensitivity of the polymers and the degree of coumarin substitution. The photosensitivity can be enhanced by the addition of sensitizers of the carbonyl type. The more powerful sensitizer seems to be p,p’-bis(dimethylamino)-benzophenone. The sensitization was attributed to a triplet-triplet energy transfer between the light-excited sensitizers and the coumarin units.

Industrie Chimique Belge published new progress about 10543-42-7. 10543-42-7 belongs to chlorides-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Chloride,Sulfonyl chlorides,Ester, name is Coumarin-6-sulfonyl chloride, and the molecular formula is C9H5ClO4S, Recommanded Product: Coumarin-6-sulfonyl chloride.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics

Karimi, Farhad published the artcilePalladium-mediated carboxylation of aryl halides (triflates) or benzyl halides using [¹³C]/[¹¹C]carbon monoxide with tetramethylammonium hydroxide or trimethylphenylammonium hydroxide, Safety of 3-Chloro-2,6-dimethoxybenzoic acid, the publication is Journal of the Chemical Society, Perkin Transactions 1 (2002), 2256-2259, database is CAplus.

[Carbonyl-¹¹C]carboxylic acids were synthesized using palladium-mediated reaction of [¹¹C]carbon monoxide with aryl halides/triflates and benzyl halides in combination with either tetramethylammonium hydroxide or trimethylphenylammonium hydroxide. The radiochem. yields were in the range 20-85%. In a typical experiment starting with 2.1 GBq[¹¹C]carbon monoxide, 0.6 GBq of HPLC-purified 1-[carbonyl-¹¹C]naphthoic acid was obtained within 25 min of the start of the carbonylation reaction (67% decay-corrected radiochem. yield). The specific radioactivity of [carbonyl-¹¹C]nicotinic acid was in the order of 750 GBq μmol^-1 using 10.0 μAh bombardment. [Carbonyl-¹³C]nicotinic acid was synthesized to verify the position of the labeling (δ 166.1) determined by ¹³C NMR.

Journal of the Chemical Society, Perkin Transactions 1 published new progress about 36335-47-4. 36335-47-4 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Carboxylic acid,Benzene,Ether, name is 3-Chloro-2,6-dimethoxybenzoic acid, and the molecular formula is C9H9ClO4, Safety of 3-Chloro-2,6-dimethoxybenzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics