Month: December 2022

Jeong, Susan published the artcileMacrocyclic Triarylethylenes via Heck Endocyclization: A System Relevant to Diazonamide Synthesis, COA of Formula: C10H11N3O3S, the publication is Journal of Organic Chemistry (1998), 63(24), 8640-8641, database is CAplus.

The author’s approach the preparation of diazonamide A (I) synthesis is described. Initial results show that Heck endocyclization can form highly functionalized lactam rings containing an imbedded 1,2-diaryl-1-(5-oxazolyl)ethylene. Thus, cross-coupling of vinylstannane II (PMB = p-methoxybenzyl) with functionalized oxazole III (prepared in 2 steps from Boc-Val-OH and aminomalononitrile tosylate) gave phenol IV in 89% yield after deprotection. Peptide coupling of IV with a protected O-benzyl-3-iodotyrosine derivative, followed by Pd-catalyzed macrocyclization gave macrocycle V, which contains the diazonamide AEF ring system.

Journal of Organic Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, COA of Formula: C10H11N3O3S.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Chen, Chaonan published the artcileSynthesis and biological activity of substituted 1,2,4-triazolo[1,5-c]pyrimidine derivatives, Name: 2-(Chloromethyl)benzonitrile, the publication is Youji Huaxue (2009), 29(2), 245-251, database is CAplus.

A method for the synthesis of the title compounds is reported here. Several 2-(benzyloxy)-7-chloro-5-(methylthio)[1,2,4]triazolo[1,5-c]pyrimidine derivatives and 2-phenoxy[1,2,4]triazolo[1,5-c]pyrimidine derivatives were designed and synthesized using substituted 4-(hydrazinyl)pyrimidine as starting material. All compounds were confirmed by elemental anal., MS, NMR. A preliminary bioassay indicated that some compounds display good herbicidal and fungicidal activity.

Youji Huaxue published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Name: 2-(Chloromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Zhang, Ming-Liang published the artcileAsymmetric Michael reaction of arylacetyl phosphonates to nitroalkenes with bifunctional amine-thiourea catalyst bearing multiple-hydrogen-bond donor: efficient construction of chiral α-substituted carboxylic ester compounds, Application In Synthesis of 5153-73-1, the publication is Tetrahedron (2016), 72(21), 2677-2682, database is CAplus.

Catalytic asym. Michael addition of arylacetyl phosphonates to nitroalkenes was achieved with a chiral bifunctional amine-thiourea bearing a multiple-hydrogen-bond donor as a catalyst. A range of α-substituted carboxylic ester compounds with contiguous tertiary stereocenters could be smoothly obtained in good yields (up to 85%) and with high to excellent diastereo- and enantioselectivities (up to >99:1 dr and 95% ee). The large scale experiment and facile synthesis of a chiral γ-butyrolactam also were demonstrated.

Tetrahedron published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C14H22O2, Application In Synthesis of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Rosowsky, Andre published the artcileMethotrexate analogs. 4. 7-Methyl derivatives of methotrexate and dichloromethotrexate. New synthesis and some biological studies, HPLC of Formula: 5098-14-6, the publication is Journal of Medicinal Chemistry (1974), 17(12), 1308-11, database is CAplus and MEDLINE.

Conversion of methotrexate (I) [59-05-2] and 3′,5′-dichloromethotrexate (II) [528-74-5] to their 7-methyl analogs III [35190-25-1] and IV [53729-18-3], resp., to prevent metabolism in vivo to the inactive 7-hydroxy derivatives resulted in marked loss of antileukemic activity in mice and in vitro and loss of inhibitory potency against purified dihydrofolate reductase [9002-03-3] from Lactobacillus casei and L1210-FR8 tumor. The lack of antitumor activity presumably resulted from impaired enzyme binding. III was prepared from 2-amino-5-chloromethyl-3-cyano-6-methylpyrazine 1-oxide [53661-20-4] and diethyl N-(p-N-methylaminobenzoyl)glutamate [2378-95-2] by the method of E. C. Taylor, et al. (1973).

Journal of Medicinal Chemistry published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C10H11N3O3S, HPLC of Formula: 5098-14-6.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Shen, Yan published the artcileCopper-catalyzed direct C-H arylation of pyridine N-oxides with arylboronic esters: one-pot synthesis of 2-arylpyridines, HPLC of Formula: 214360-44-8, the publication is Chemical Communications (Cambridge, United Kingdom) (2014), 50(33), 4292-4295, database is CAplus and MEDLINE.

The first example of the copper-catalyzed direct C-H arylation of pyridine N-oxides with arylboronic esters has been developed, leading to a wide range of 2-arylpyridines in a one-pot synthesis with moderate to good yields without an addnl. reductant. This transformation allows for rapid access to a variety of 2-arylpyridines using an inexpensive catalytic system that would be more difficult to access with traditional methods. Thus, this method represents a simple and practical procedure to access 2-arylpyridines.

Chemical Communications (Cambridge, United Kingdom) published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C44H28ClFeN4, HPLC of Formula: 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Chang, Dan published the artcileMetal-Free Synthesis and Photophysical Properties of 1,2,4-Triarylpyrroles, HPLC of Formula: 5153-73-1, the publication is Journal of Organic Chemistry (2021), 86(1), 110-127, database is CAplus and MEDLINE.

A three-component reaction has been developed for the construction of multiaryl-substituted pyrrole derivatives from arylketones, amines, and nitrovinylarenes under metal-free conditions. Hence, homologous 1,2,4-triaryl-substituted pyrrole products were obtained in good to high yields. Furthermore, 2,3,5-triaryl-substituted pyrroles were selectively formed in the absence of nitrovinylarenes. The photophys. properties of some pyrrole products have been investigated to show good aggregation-induced emission (AIE) activity.

Journal of Organic Chemistry published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, HPLC of Formula: 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Shey, Chun Feng published the artcileSynthesis of 2,4-diamino-6-substituted pteridine, Product Details of C10H11N3O3S, the publication is Shida Xuebao (Taipei) (1984), 631-43, database is CAplus.

Title compounds I (R = Cl, OH), intermediates for methotrexate, were prepared Thus, cyclocondensation of 2,4,5,6-tetraaminopyrimidine with CO(CH₂OH)₂ gave I (R = OH) whereas cyclocondensation of 2-amino-3-cyano-5-chloromethylpyrazine with guanidine gave I (R = Cl).

Shida Xuebao (Taipei) published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C25H47NO8, Product Details of C10H11N3O3S.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Mohlmann, Lennart published the artcileOrganocatalytic Enantioselective Synthesis of Tetrahydrofluoren-9-ones via Vinylogous Michael Addition/Henry Reaction Cascade of 1,3-Indandione-Derived Pronucleophiles, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2016), 18(4), 688-691, database is CAplus and MEDLINE.

An unprecedented organocatalytic enantioselective vinylogous Michael addition and Henry cyclization cascade is presented for the synthesis of highly substituted tetrahydrofluoren-9-ones employing novel 1,3-indandione-derived pronucleophiles and nitroalkenes. Following a very simple protocol, a wide range of products were obtained in good to excellent yields and with excellent enantioinduction (43-98% yields, up to 98% ee). The reaction proceeded with excellent diastereocontrol despite the simultaneous generation of four stereogenic centers. Surprisingly, when 2-(1-phenylethylidene)-1H-indandione was used as a pronucleophile, no cyclization was observed, and only Michael addition adducts were furnished in very good yields and excellent enantioselectivities.

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Safety of (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ma, Zhuang published the artcileStable and reusable Ni-based nanoparticles for general and selective hydrogenation of nitriles to amines, Application In Synthesis of 238088-16-9, the publication is Chemical Science (2022), 13(36), 10914-10922, database is CAplus.

Silica supported ultrasmall Ni-nanoparticles allow for general and selective hydrogenation of all kinds of nitriles to primary amines under mild conditions. By calcination of a template material generated from Ni(II)nitrate and colloidal silica under air and subsequent reduction in the presence of mol. hydrogen the optimal catalyst was prepared The prepared supported nanoparticles are stable, was conveniently used and easily recycled. The applicability of the optimal catalyst material was shown by hydrogenation of >110 diverse aliphatic and aromatic nitriles including functionalized and industrially relevant substrates. Challenging heterocyclic nitriles, specifically cyanopyridines, provided the corresponding primary amines in good to excellent yields. The resulting amines serve as important precursors and intermediates for the preparation of numerous life science products and polymers.

Chemical Science published new progress about 238088-16-9. 238088-16-9 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Aliphatic cyclic hydrocarbon,Boronic Acids,Boronate Esters, name is 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butanenitrile, and the molecular formula is C10H18BNO2, Application In Synthesis of 238088-16-9.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Gadd, Adam J. R. published the artcileHigh potency of lipid conjugated TLR7 agonist requires nanoparticulate or liposomal formulation, COA of Formula: C13H7Cl2N5, the publication is European Journal of Pharmaceutical Sciences (2018), 268-276, database is CAplus and MEDLINE.

Here, we studied the effect of formulation on potency of a 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine (DOPE) conjugated TLR7 agonist (DOPE-TLR7a) alongside assessing phys. form using Dynamic Light Scattering (DLS), Nanosight Particle Tracking (NTA) anal. and Small Angle X-ray Scattering (SAXS). A very high potency of DOPE-TLR7a conjugate (EC₅₀ around 9 nM) was observed either when prepared by direct dilution from DMSO or when formulated into 400-700 nm large multilamella liposomes containing dimethyldioctadecylammonium bromide salt (DDA) and DOPE. When prepared by dissolution in DMSO followed by dilution in aqueous culture medium, 93 ± 5 nm nanoparticles were formed. Without dilution from solution in DMSO, no nanoparticles were observed and no immunostimulatory activity could be detected without this formulation step. SAXS anal. of the conjugate after DMSO dissolution/water dilution revealed a lamellar order with a layer spacing of 68.7 Å, which correlates with arrangement in groups of 3 bilayers. The addition of another immunostimulatory glycolipid, trehalose-6,6-dibehenate (TDB), to DOPE:DDA liposomes gave no further increase in immunostimulatory activity beyond that provided by incorporating DOPE-TLR7a. Given the importance of nanoparticle or liposomal formulation for activity, we conclude that the major mechanism for increased potency when TLR7 agonists are conjugated to macromols. is through alteration of phys. form.

European Journal of Pharmaceutical Sciences published new progress about 115204-76-7. 115204-76-7 belongs to nitriles-buliding-blocks, auxiliary class 5.6_Aromatics,Purines, name is 4-((2,6-Dichloro-9H-purin-9-yl)methyl)benzonitrile, and the molecular formula is C13H7Cl2N5, COA of Formula: C13H7Cl2N5.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts