Tag: 100-200

Structure-based design of novel guanidine/benzamidine mimics: potent and orally bioavailable factor Xa inhibitors as novel anticoagulants was written by Lam, Patrick Y. S.;Clark, Charles G.;Li, Renhua;Pinto, Donald J. P.;Orwat, Michael J.;Galemmo, Robert A.;Fevig, John M.;Teleha, Christopher A.;Alexander, Richard S.;Smallwood, Angela M.;Rossi, Karen A.;Wright, Matthew R.;Bai, Stephen A.;He, Kan;Luettgen, Joseph M.;Wong, Pancras C.;Knabb, Robert M.;Wexler, Ruth R.. And the article was included in Journal of Medicinal Chemistry in 2003.Computed Properties of C9H8N2 This article mentions the following:

As part of an ongoing effort to prepare orally active factor Xa inhibitors using structure-based drug design techniques and mol. recognition principles, a systematic study has been performed on the pharmacokinetic profile resulting from replacing the benzamidine in the P1 position with less basic benzamidine mimics or neutral residues. It is demonstrated that lowering the pK_a of the P1 ligand resulted in compounds (3-benzylamine, 15a; 1-aminoisoquinoline, 24a; 3-aminobenzisoxazole, 23a; 3-phenylcarboxamide, 22b; and 4-methoxyphenyl, 22a) with improved pharmacokinetic features mainly as a result of decreased clearance, increased volume of distribution, and enhanced oral absorption. This work resulted in a series of potent and orally bioavailable factor Xa inhibitors that ultimately led to the discovery of SQ311, 24a. SQ311, which utilizes a 1-aminoisoquinoline as the P1 ligand, inhibits factor Xa with a K_i of 0.33 nM and demonstrates both good in vivo antithrombotic efficacy and oral bioavailability. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Computed Properties of C9H8N2).

Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. Quinoline is a catabolite of tryptophan, the basic structure of some antihypertensive drugs, such as the peripheral vasodilators prazosin and doxazosin. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Computed Properties of C9H8N2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

A new synthesis of 1-alkyl(aryl)-4-isoquinolinols was written by Constable, Kevin P.;Carroll, F. Ivy. And the article was included in Heterocyclic Communications in 1996.Category: isoquinoline This article mentions the following:

A new synthesis of 4-isoquinolinol and 1-methyl-4-isoquinolinol and its application to the syntheses of other 1-alkyl(aryl)-4-isoquinolinols I (R = Et, CHMe₂, Ph) from 4-bromoisoquinoline was developed. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5Category: isoquinoline).

4-Methoxyisoquinoline (cas: 36034-54-5) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. The Pomeranz–Fritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.Category: isoquinoline

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Quantum-mechanical study of the reactivity of π-electron systems in excited singlet and triplet states. III. Electronic structure of amino derivatives of nitrogen-containing heterocycles in excited singlet and triplet states was written by Tyutyulkov, Nikolai;Hiebaum, G.. And the article was included in Theoretica Chimica Acta in 1969.Quality Control of Isoquinolin-7-amine This article mentions the following:

The spectra and charge distribution in the ground and excited states of a series of amino derivatives of heterocycles containing N have been studied by the configuration-interaction method. Excitation of the mol. is accompanied by considerable charge transfer from the amino N atom to the heterocycle. This transfer is particularly pronounced in the fluorescent state. The elec. moments calculated by assuming σ-π separation are in very good agreement with exptl. data. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Quality Control of Isoquinolin-7-amine).

Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. Quinoline is a catabolite of tryptophan, the basic structure of some antihypertensive drugs, such as the peripheral vasodilators prazosin and doxazosin. Other industrial applications include their use as corrosion inhibitors, preservatives, and as solvents for resins and terpenes.Quality Control of Isoquinolin-7-amine

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Theoretical calculations on aminoquinolines and aminoisoquinolines was written by Dasgupta, Molina;Basu, Sadhan. And the article was included in Journal de Chimie Physique et de Physico-Chimie Biologique in 1961.Reference of 23707-37-1 This article mentions the following:

The Hückel method is used. The exptl. pKs of these compounds are related neither to elec. charge on the ring N nor to localization energy on protonation. The force constant of the exocyclic CN bond can be calculated satisfactorily with the equation of Coulson and Longuet-Higgins (CA 42, 1489i). The length of this bond, calculated with the equation of Badger (CA 28, 2996⁶), is well correlated with its bond order. The charge d. on the ring N atom correlates better with the exptl. N-H force constant than does the charge d. on the amino N atom. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Reference of 23707-37-1).

Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Reference of 23707-37-1

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Structure-Photochemical Function Relationships in Nitrogen-Containing Heterocyclic Aromatic Photobases Derived from Quinoline was written by Alamudun, Sophya F.;Tanovitz, Kyle;Fajardo, April;Johnson, Kaitlind;Pham, Andy;Jamshidi Araghi, Tina;Petit, Andrew S.. And the article was included in Journal of Physical Chemistry A in 2020.COA of Formula: C10H9NO This article mentions the following:

Photobases are compounds that become strong bases after electronic excitation. Recent exptl. studies have highlighted the photobasicity of the 5-R quinoline compounds, demonstrating a strong substituent dependence to the pK_a^*. In this paper, we describe our systematic study of how the thermodn. driving force for photobasicity is tuned through substituents in four families of nitrogen-containing heterocyclic aromatics We show that substituent position and identity both significantly impact the pK_a^*. We demonstrate that the substituent effects are additive and identify many disubstituted compounds with substantially greater photobasicity than the most photobasic 5-R quinoline compound identified previously. We show that the addition of a second fused benzene ring to quinoline, along with two electron-donating substituents, lowers the S₀ â†?S_PBS vertical excitation energy into the visible region while still maintaining a pK_a^* > 14. Overall, the structure-function relationships developed in this study provide new insights to guide the development of new photocatalysts that employ photobasicity. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5COA of Formula: C10H9NO).

4-Methoxyisoquinoline (cas: 36034-54-5) belongs to isoquinoline derivatives. Being an analog of pyridine, isoquinoline is a weak base, with a pKa of 5.14. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3.COA of Formula: C10H9NO

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands was written by Ingoglia, Bryan T.;Buchwald, Stephen L.. And the article was included in Organic Letters in 2017.Formula: C10H9NO This article mentions the following:

Palladium-based oxidative addition complexes derived from aryl triflates or bromides and the bulky phosphine ligands AlPhos and t-BuBrettPhos were prepared as easily prepared, air-stable, and effective precatalysts for C-N, C-O, and C-F cross-coupling reactions with a variety of (hetero)arenes. These complexes offer a convenient alternative to previously developed classes of precatalysts, particularly in the case of the bulkiest biarylphosphine ligands, for which palladacycle-based precatalysts do not readily form. The structure of an AlPhos (trifluoromethylphenyl)palladium triflate complex benzene solvate was determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5Formula: C10H9NO).

4-Methoxyisoquinoline (cas: 36034-54-5) belongs to isoquinoline derivatives. Being an analog of pyridine, isoquinoline is a weak base, with a pKa of 5.14. The Pomeranz–Fritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.Formula: C10H9NO

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Photochemistry of methoxy-substituted quinoline and isoquinoline N-oxides was written by Albini, Angelo;Fasani, Elisa;Dacrema, Lucia Maggi. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1980.Reference of 36034-54-5 This article mentions the following:

Irradiation of methoxyquinoline and -isoquinoline N-oxides gave a variety of photoisomers as well as deoxygenation and secondary reaction products, the nature of the products being dependent on the solvent and the position of the -OMe group. E.g., the irradiation of I (R = H, R¹ = OMe) (medium-pressure Hg vapor lamp, 15°) gave 83% II in H₂O whereas in C₆H₆ 50% III (R = H, R¹ = OMe) was obtained; however I (R = OMe, R¹ = H) gave, under the same conditions, o-HOC₆H₄CH:CHNHCO₂Me and IV (22 and 22%, resp.) in water, and III (R = OMe, R¹ = H) (40%) in C₆H₁₂. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5Reference of 36034-54-5).

4-Methoxyisoquinoline (cas: 36034-54-5) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. The discovery of chloroquine, the most well-known drug containing this stent, has helped bring about decades of malaria control and treatment.Reference of 36034-54-5

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

N-Methylation of amines with methanol catalyzed by a Cp*Ir complex bearing a functional 2,2′-bibenzimidazole ligand was written by Liang, Ran;Li, Shun;Wang, Rongzhou;Lu, Lei;Li, Feng. And the article was included in Organic Letters in 2017.Electric Literature of C9H8N2 This article mentions the following:

A new type of Cp*Ir complex bearing a functional 2,2′-bibenzimidazole ligand, [Cp^*IrCl[2,2′-(C₇H₅N₂)₂]] was designed, synthesized, and found to be a highly effective and general catalyst for the N-methylation of a variety of amines with methanol in the presence of a weak base (0.3 equiv of Cs₂CO₃), giving N-methylamines with high chemoselectivity. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Electric Literature of C9H8N2).

Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. Other industrial applications include their use as corrosion inhibitors, preservatives, and as solvents for resins and terpenes.Electric Literature of C9H8N2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Photoredox-Catalyzed Redox-Neutral Minisci C-H Formylation of N-Heteroarenes was written by Dong, Jianyang;Wang, Xiaochen;Song, Hongjian;Liu, Yuxiu;Wang, Qingmin. And the article was included in Advanced Synthesis & Catalysis in 2020.Reference of 36034-54-5 This article mentions the following:

A protocol for redox-neutral Minisci C-H formylation of N-heteroarenes using 1,3-dioxoisoindolin-2-yl 2,2-diethoxyacetate as a formyl equivalent at room temp was reported. This scalable benchtop protocol offered a distinct advantage over traditional reductive carbonylation and Minisci C-H formylation methods in not requiring the use of carbon monoxide, pressurized gas, a stoichiometric reductant, or a stoichiometric oxidant. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5Reference of 36034-54-5).

4-Methoxyisoquinoline (cas: 36034-54-5) belongs to isoquinoline derivatives. Quinoline is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. They are also used to make oil-soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. Reference of 36034-54-5

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Discovery of Phenylglycine Lactams as Potent Neutral Factor VIIa Inhibitors was written by Wurtz, Nicholas R.;Parkhurst, Brandon L.;Jiang, Wen;DeLucca, Indawati;Zhang, Xiaojun;Ladziata, Vladimir;Cheney, Daniel L.;Bozarth, Jeffrey R.;Rendina, Alan R.;Wei, Anzhi;Luettgen, Joseph M.;Wu, Yiming;Wong, Pancras C.;Seiffert, Dietmar A.;Wexler, Ruth R.;Priestley, E. Scott. And the article was included in ACS Medicinal Chemistry Letters in 2016.Application In Synthesis of 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one This article mentions the following:

Inhibitors of Factor VIIa (FVIIa), a serine protease in the clotting cascade, have shown strong antithrombotic efficacy in preclin. thrombosis models with minimal bleeding liabilities. Discovery of potent, orally active FVIIa inhibitors has been largely unsuccessful because known chemotypes have required a highly basic group in the S1 binding pocket for high affinity. A recently reported fragment screening effort resulted in the discovery of a neutral heterocycle, 7-chloro-3,4-dihydroisoquinolin-1(2H)-one, that binds in the S1 pocket of FVIIa and can be incorporated into a phenylglycine FVIIa inhibitor. Optimization of this P1 binding group led to the first series of neutral, permeable FVIIa inhibitors with low nanomolar potency. In the experiment, the researchers used many compounds, for example, 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one (cas: 22245-96-1Application In Synthesis of 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one).

7-Nitro-3,4-dihydroisoquinolin-1(2H)-one (cas: 22245-96-1) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Application In Synthesis of 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem