Tag: 100-200

Name: 3-(Methoxycarbonyl)benzoic acidOn September 1, 2019 ,《Design and synthesis of 3-aminophthalazine derivatives and structural analogues as PDE5 inhibitors: anti-allodynic effect against neuropathic pain in a mouse model》 was published in European Journal of Medicinal Chemistry. The article was written by Bollenbach, Maud; Lugnier, Claire; Kremer, Melanie; Salvat, Eric; Megat, Salim; Bihel, Frederic; Bourguignon, Jean-Jacques; Barrot, Michel; Schmitt, Martine. The article contains the following contents:

Herein, a series of aminophthalazine I [R = H, Ph, 1-piperidyl, etc.; R1 = H, CF3; R2 = 3-ClC6H4NH, 4-MeOC6H4CH2NH, Ph(CH2)2NH, etc.] and aminoindazole derivatives II [R3 = H, Cl, CF3; R4 = H, Me, Ph, etc.; R5 = 3-ClC6H4, 4-MeOC6H4CH2, 3-F-4-MeOC6H3CH2, etc.] were synthesized and evaluated for their inhibitory activity toward PDE5. Selectivity profiles towards other PDE1-4 isoenzymes, water solubility and stability in acidic medium of the most potent PDE5 inhibitors were determined and the aminophthalazine I [R = Ph, R1 = CF3, R2 = 4-OMeC6H4CH2NH] and its mimetic compound II [R3 = CF3, R4 = 3-pyridyl, R5 = 4-OMeC6H4CH2NH] were evaluated in comparison to MY 5445 in vivo in a model of neuropathic pain induced by sciatic nerve cuffing in mice (3 and 0.5 mg/kg, i.p. twice a day). Both compounds showed the same efficacy on neuropathic allodynia as MY 5445 and thus produced a significant relief of mech. hypersensitivity after 12 days of treatment. In the experimental materials used by the author, we found 3-(Methoxycarbonyl)benzoic acid(cas: 1877-71-0Name: 3-(Methoxycarbonyl)benzoic acid)

3-(Methoxycarbonyl)benzoic acid(cas: 1877-71-0) belongs to esters. Esters are more polar than ethers but less polar than alcohols. Name: 3-(Methoxycarbonyl)benzoic acid They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

《A Multifunctional Reagent Designed for the Site-Selective Amination of Pyridines》 was published in Journal of the American Chemical Society in 2020. These research results belong to Fier, Patrick S.; Kim, Suhong; Cohen, Ryan D.. Application of 36016-38-3 The article mentions the following:

The development of a multifunctional reagent for the direct conversion of pyridines to Boc-protected 2-aminopyridines such as I [R = H, 3-Br, 4-Ph, etc.] with exquisite site selectivity and chemoselectivity was reported. The novel reagent was prepared on 200g scale in a single step, reacted in title reaction under mild conditions without precautions toward air or moisture, and is tolerant of nearly all common functionality. Exptl. and in situ spectroscopic monitoring techniques provided detailed insights and unexpected findings for the unique reaction mechanism.N-tert-Butoxycarbonylhydroxylamine(cas: 36016-38-3Application of 36016-38-3) was used in this study.

N-tert-Butoxycarbonylhydroxylamine(cas: 36016-38-3) belongs to anime. Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.Application of 36016-38-3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

《Hydrophobic Pockets of HPMC Enable Extremely Short Reaction Times in Water》 was published in ACS Sustainable Chemistry & Engineering in 2020. These research results belong to Petkova, Desislava; Borlinghaus, Niginia; Sharma, Sudripet; Kaschel, Johannes; Lindner, Tanja; Klee, Johanna; Jolit, Anais; Haller, Vanessa; Heitz, Stephanie; Britze, Katarina; Dietrich, Justin; Braje, Wilfried M.; Handa, Sachin. Application of 4248-19-5 The article mentions the following:

A methodol. for formation of ligated ultrasmall in-situ generated Pd nanoparticles in the hydrophobic pockets of benign cellulose derivative hydroxypropyl methylcellulose (HPMC) for chem. reactions to proceed very fast in water under mild reaction conditions was reported. Unprecedented short reaction times were exemplified for the Buchwald-Hartwig amination reaction of aryl bromides and aryl amines using in-situ generated Pd nanoparticles in aqueous HMPC solution to afford substituted aryl amines RNHR1 [R = 1-naphthyl, 3-MeC6H4, 2-MeOC6H4, etc.; R1 = Ph, 4-MeC6H4, 1-naphthyl, etc.]. In addition, very short reaction times were also demonstrated for the peptide coupling of carboxylic acids and amines using in-situ generated Pd nanoparticles in aqueous HMPC solution to afford aryl amides R2C(O)NR3R4 [R2 = Bn, 4-ClC6H4, 4-BrC6H4, etc.; R3 = OMe, n-hexyl, 3,5-(Me)2C6H3, etc.; R4 = H, Me, etc.]. After reading the article, we found that the author used tert-Butyl carbamate(cas: 4248-19-5Application of 4248-19-5)

tert-Butyl carbamate(cas: 4248-19-5) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Application of 4248-19-5

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The author of 《Palladium-Catalyzed Amidation and Amination of (Hetero)aryl Chlorides under Homogeneous Conditions Enabled by a Soluble DBU/NaTFA Dual-Base System》 were Beutner, Gregory L.; Coombs, John R.; Green, Rebecca A.; Inankur, Bahar; Lin, Dong; Qiu, Jun; Roberts, Frederick; Simmons, Eric M.; Wisniewski, Steven R.. And the article was published in Organic Process Research & Development in 2019. Formula: C5H11NO2 The author mentioned the following in the article:

The palladium-catalyzed coupling of aryl and heteroaryl chlorides with primary amides under mild homogeneous reaction conditions is reported. Successful C-N coupling is enabled using a unique “”dual-base”” system consisting of DBU and NaTFA, which serve as proton acceptor and halide scavenger, resp., using low catalyst loadings (0.5 mol %) with readily available, air-stable palladium precatalysts. The DBU/NaTFA system also enables the room-temperature coupling of primary aryl amines with aryl chlorides and is tolerant of a variety of base-sensitive functional groups. In the experimental materials used by the author, we found tert-Butyl carbamate(cas: 4248-19-5Formula: C5H11NO2)

tert-Butyl carbamate(cas: 4248-19-5) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Formula: C5H11NO2

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The author of 《Synthesis, Electronic Spectroscopy, and Photochemistry of Methacrolein Oxide: A Four-Carbon Unsaturated Criegee Intermediate from Isoprene Ozonolysis》 were Vansco, Michael F.; Marchetti, Barbara; Trongsiriwat, Nisalak; Bhagde, Trisha; Wang, Guanghan; Walsh, Patrick J.; Klippenstein, Stephen J.; Lester, Marsha I.. And the article was published in Journal of the American Chemical Society in 2019. Synthetic Route of C8H14O4 The author mentioned the following in the article:

Ozonolysis of isoprene, a most abundant volatile organic compound in the Earth atm., generates the four-carbon unsaturated, methacrolein oxide (MACR-oxide), Criegee intermediate. Initial laboratory synthesis and direct detection of MACR-oxide was achieved by reaction of photolytically-generated, resonance-stabilized iodoalkene radicals with O. MACR-oxide was characterized on its first π* ← π electronic transition using a ground-state depletion method. MACR-oxide exhibited a broad UV-vis spectrum peak at 380 nm with weak oscillatory structure at long wavelengths ascribed to vibrational resonances. Complementary theory predicted two strong π* ← π transitions from extended conjugation across MACR-oxide with overlapping contributions from its four conformers. Electronic promotion to the 11ππ* state agreed well with exptl. data and resulted in non-adiabatic coupling and prompt release of O 1D products observed as anisotropic velocity-map images. This UV-visible detection scheme enables the study of its unimol. and bimol. reactions under thermal conditions relevant to the atm. In the experiment, the researchers used Diethyl 2-methylmalonate(cas: 609-08-5Synthetic Route of C8H14O4)

Diethyl 2-methylmalonate(cas: 609-08-5) belongs to aliphatic hydrocarbons. Aliphatic hydrocarbons belong to the most abundant fraction in crude oil. Aliphatics molecules are linear or branched open-chain structures such as n-alkanes, isoalkanes, cycloalkanes (naphthenes), terpenes and steranes.Synthetic Route of C8H14O4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 2017,Barlaam, Bernard; Cosulich, Sabina; Fitzek, Martina; Germain, Herve; Green, Stephen; Hanson, Lyndsey L.; Harris, Craig S.; Hancox, Urs; Hudson, Kevin; Lambert-van der Brempt, Christine; Lamorlette, Maryannick; Magnien, Francoise; Ouvry, Gilles; Page, Ken; Ruston, Linette; Ward, Lara; Delouvrie, Benedicte published 《Discovery of a novel aminopyrazine series as selective PI3Kα inhibitors》.Bioorganic & Medicinal Chemistry Letters published the findings.Computed Properties of C4H7NO2S The information in the text is summarized as follows:

We report the discovery of a novel aminopyrazine series of PI3Kα inhibitors, designed by hybridizing two known scaffolds of PI3K inhibitors. We describe the progress achieved from the first compounds plagued with poor general kinase selectivity to compounds showing high selectivity for PI3Kα over PI3Kβ and excellent general kinase selectivity. This effort culminated with the identification of compound 5 displaying high potency and selectivity, and suitable physiochem. and pharmacokinetic properties for oral administration. In vivo, compound I showed good inhibition of tumor growth (86% tumor growth inhibition at 50 mg/kg twice daily orally) in the MCF7 xenograft model in mice. The results came from multiple reactions, including the reaction of Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1Computed Properties of C4H7NO2S)

Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Computed Properties of C4H7NO2S

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 2016,Read, Cai; Fitzpatrick, Christopher M.; Yang, Peiran; Kuc, Rhoda E.; Maguire, Janet J.; Glen, Robert C.; Foster, Richard E.; Davenport, Anthony P. published 《Cardiac action of the first G protein biased small molecule apelin agonist》.Biochemical Pharmacology (Amsterdam, Netherlands) published the findings.Computed Properties of C8H6FNO4 The information in the text is summarized as follows:

Apelin peptide analogs displaying bias towards G protein signalling pathways have beneficial cardiovascular actions compared with the native peptide in humans in vivo. Our aim was to determine whether small mol. agonists could retain G protein bias. We have identified a biased small mol., CMF-019 (I), and characterised it in vitro and in vivo. In competition radioligand binding experiments in heart homogenates, CMF-019 bound to the human, rat and mouse apelin receptor with high affinity (pKi = 8.58 ± 0.04, 8.49 ± 0.04 and 8.71 ± 0.06 resp.). In cell-based functional assays, whereas, CMF-019 showed similar potency for the Gαi pathway to the endogenous agonist [Pyr1]apelin-13 (pD2 = 10.00 ± 0.13 vs 9.34 ± 0.15), in β-arrestin and internalisation assays it was less potent (pD2 = 6.65 ± 0.15 vs 8.65 ± 0.10 and pD2 = 6.16 ± 0.21 vs 9.28 ± 0.10 resp.). Anal. of these data demonstrated a bias of ∼400 for the Gαi over the β-arrestin pathway and ∼6000 over receptor internalisation. CMF-019 was tested for in vivo activity using i.v. injections into anesthetized male Sprague-Dawley rats fitted with a pressure-volume catheter in the left ventricle. CMF-019 caused a significant increase in cardiac contractility of 606 ± 112 mmHg/s (p < 0.001) at 500 nmol. CMF-019 is the first biased small mol. identified at the apelin receptor and increases cardiac contractility in vivo. We have demonstrated that Gαi over β-arrestin/internalisation bias can be retained in a non-peptide analog and predict that such bias will have the therapeutic benefit following chronic use. CMF-019 is suitable as a tool compound and provides the basis for design of biased agonists with improved pharmacokinetics for treatment of cardiovascular conditions such as pulmonary arterial hypertension. The experimental process involved the reaction of Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9Computed Properties of C8H6FNO4)

Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9) belongs to methyl benzoate. Methyl benzoate reacts at both the ring and the ester, depending on the substrate. Electrophiles attack the ring, illustrated by acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate.Computed Properties of C8H6FNO4Methyl 4-fluoro-3-nitrobenzoate is used to prepare dimethyl 3-nitro-3′,4-oxydibenzoate by reacting with 3-hydroxy-benzoic acid methyl ester.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 2008,Tredwell, Matthew; Luft, Jennifer A. R.; Schuler, Marie; Tenza, Kenny; Houk, Kendall N.; Gouverneur, Veronique published 《Fluorine-directed diastereoselective iodocyclizations》.Angewandte Chemie, International Edition published the findings.Electric Literature of C4H8O3 The information in the text is summarized as follows:

β-Fluorinated lactones and tetrahydrofurans are synthesized by iodocyclization of various allylic fluorides. The fluorine substituent acts as a highly efficient syn-stereodirecting group for the ring closure. The exptl. results combined with theor. studies provide evidence in support of an inside fluoro effect to account for the sense and level of stereocontrol of these reactions. In the experiment, the researchers used Methyl 3-hydroxypropanoate(cas: 6149-41-3Electric Literature of C4H8O3)

Methyl 3-hydroxypropanoate(cas: 6149-41-3) belongs to esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Electric Literature of C4H8O3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In 2003,Hollowood, Christopher J.; Yamanoi, Shigeo; Ley, Steven V. published 《Use of π-allyltricarbonyliron lactone complexes in the synthesis of taurospongin A: a potent inhibitor of DNA polymerase β and HIV reverse transcriptase》.Organic & Biomolecular Chemistry published the findings.Computed Properties of C4H8O3 The information in the text is summarized as follows:

The total synthesis of taurospongin A (I) by two new approaches has been achieved where π-allyltricarbonyliron lactone complexes have been used to control highly stereoselective additions of the . In the experiment, the researchers used Methyl 3-hydroxypropanoate(cas: 6149-41-3Computed Properties of C4H8O3)

Methyl 3-hydroxypropanoate(cas: 6149-41-3) belongs to esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Computed Properties of C4H8O3

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Chahal, Mandeep K.; Payne, Daniel T.; Matsushita, Yoshitaka; Labuta, Jan; Ariga, Katsuhiko; Hill, Jonathan P. published an article on January 6 ,2020. The article was titled 《Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis》, and you may find the article in European Journal of Organic Chemistry.Application of 30414-53-0 The information in the text is summarized as follows:

A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens having increased intramol. hydrogen-bond donor distances is reported. Oxoporphyrinogens are highly non-planar rigid macrocycles containing a multiple hydrogen bond-forming binding site. In this work, we describe the first example of non-planar OxPs as hydrogen-bond donor catalysts prepared using a mol. engineering approach of the binding site for dual activation of substrates. The introduction of β-substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4-conjugate additions and sulfa-Michael additions, as well as, Henry and aza-Henry reactions at low catalyst loadings (≤ 1 mol-%) under mild conditions (e.g., catalyst I). Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi-functional activation of both substrates through hydrogen-bonding interactions. The experimental process involved the reaction of Methyl 3-oxovalerate(cas: 30414-53-0Application of 30414-53-0)

Methyl 3-oxovalerate(cas: 30414-53-0) belongs to ketone compounds. Ketone compounds have important physiological properties. They are found in several sugars and in compounds for medicinal use, including natural and synthetic steroid hormones. Molecules of the anti-inflammatory agent cortisone contain three ketone groups.Application of 30414-53-0

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics