Day: February 23, 2023

Fasudil dichloroacetate (FDCA), an orally available agent with potent therapeutic efficiency on monocrotaline-induced pulmonary arterial hypertension rats was written by Qi, Lei;Lv, Tian;Cheng, Yusheng;Yu, Min;Han, Honghao;Kong, Hui;Xie, Weiping;Wang, Hong;Zhang, Yihua;Huang, Zhangjian. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Synthetic Route of C14H18ClN3O2S This article mentions the following:

Given the therapeutic efficacy of fasudil hydrochloride (F) and dichloroacetate (DCA) on pulmonary arterial hypertension (PAH), a new salt fasudil dichloroacetate (FDCA) was designed, synthesized and biol. evaluated. FDCA exhibited comparable ROCK II inhibitory activity relative to fasudil hydrochloride, and suppressed the expression of TNF-伪 and IL-6 in both PDGF-BB and hypoxia-treated pulmonary arterial smooth muscle cells (PASMCs) and endothelial cells (PAECs). Significantly, FDCA lowered mean pulmonary artery pressure (mPAP) and right ventricular systolic pressure (RVSP), and decreased right ventricular hypertrophy (RVH) in monocrotaline (MCT)-induced PAH rats. Meanwhile, FDCA remarkably decreased pulmonary artery medial thickness (PAMT) and hyperplasia, restoring the elasticity of elastic fiber, reduced cardiac hypertrophy, and attenuated fibrosis of heart and lung. Collectively, FDCA exhibited triple activities of pulmonary vasodilation, vascular remodeling inhibition and RVH inhibition, suggesting that it may be a promising agent for PAH intervention. In the experiment, the researchers used many compounds, for example, 5-((1,4-Diazepan-1-yl)sulfonyl)isoquinoline hydrochloride (cas: 105628-07-7Synthetic Route of C14H18ClN3O2S).

5-((1,4-Diazepan-1-yl)sulfonyl)isoquinoline hydrochloride (cas: 105628-07-7) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. The Pomeranz鈥揊ritsch 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.Synthetic Route of C14H18ClN3O2S

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Synthesis and Radioligand Binding Studies of C-5- and C-8-Substituted 1-(3,4-Dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums as SK Channel Blockers Related to N-Methyl-laudanosine and N-Methyl-noscapine was written by Graulich, Amaury;Scuvee-Moreau, Jacqueline;Seutin, Vincent;Liegeois, Jean-Francois. And the article was included in Journal of Medicinal Chemistry in 2005.COA of Formula: C9H5BrN2O2 This article mentions the following:

The synthesis and the ¹²⁵I-apamin binding studies of some C(5)- and C(8)-substituted 1-(3,4-dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums and 1-(3,4-dimethoxybenzyl)-6,6-dimethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridiniums were performed in order to find a reversible and selective SK channel blocker structurally related to N-methyllaudanosine and N-methylnoscapine. A bulky alkyl substituent in the C-8 position of the tetrahydroisoquinoline produces a clear increase in the affinity for the apamin sensitive binding sites. The presence of an electron-withdrawing group in the C-5 and C-8 positions is not a suitable substitution for the affinity of drugs structurally related to N-methyl-laudanosine. Thiophene analogs and 8-methoxy derivatives possess a poor affinity for the apamin sensitive binding sites. Electrophysiol. studies performed with the most effective compound showed a blockade of the apamin sensitive afterhyperpolarization in rat dopaminergic neurons. In the experiment, the researchers used many compounds, for example, 5-Bromo-8-nitroisoquinoline (cas: 63927-23-1COA of Formula: C9H5BrN2O2).

5-Bromo-8-nitroisoquinoline (cas: 63927-23-1) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. The Pomeranz鈥揊ritsch 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.COA of Formula: C9H5BrN2O2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Synthesis and cytotoxicity screening of derivatives of the simplified ecteinascidin pentacyclic skeleton as anticancer agents was written by Guo, Ju;Yang, Yang;Wang, Nan;Liu, Zhanzhu. And the article was included in Tetrahedron Letters in 2018.COA of Formula: C10H7NO2 This article mentions the following:

A series of new ecteinascidin pentacyclic-derived compounds bearing aryl carboxylic amide side chains at C-22, I (R = 4-FC₆H₄, 2-bromonaphthalen-6-yl, 2-thienyl, etc.) have been designed and synthesized. The cytotoxicity evaluation confirmed their potent antitumor activity by use of eight different cell lines. Studies on the structure-activity relationship of them showed that the chem. structure of C-22 pendants have great effects on the tumor-killing activity. Notably, compounds I (R = 3-chlorobenzo[b]thien-2-yl, 3-chloro-6-fluorobenzo[b]thien-2-yl, 3-chloro-6-ethylbenzo[b]thien-2-yl) with benzo[b]thiophene-2-carboxamide pendants exhibited excellent broad-spectrum antitumor activity with the low IC₅₀ values of 10^-7M. In the experiment, the researchers used many compounds, for example, Isoquinoline-1-carboxylic acid (cas: 486-73-7COA of Formula: C10H7NO2).

Isoquinoline-1-carboxylic acid (cas: 486-73-7) belongs to isoquinoline derivatives. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. 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: C10H7NO2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Asymmetric Transfer Hydrogenation in Thermomorphic Microemulsions Based on Ionic Liquids was written by Hejazifar, Mahtab;Palvoelgyi, Adam Mark;Bitai, Jacqueline;Lanaridi, Olga;Bica-Schroeder, Katharina. And the article was included in Organic Process Research & Development in 2019.Electric Literature of C15H13N This article mentions the following:

A thermomorphic ionic-liquid-based microemulsion system was successfully applied for the Ru-catalyzed asym. transfer hydrogenation of ketones. On the basis of the temperature-dependent multiphase behavior of the targeted microemulsion, simple product separation as well as catalyst recycling could be realized. The use of water-soluble ligands improved the immobilization of the catalyst in the microemulsion phase and significantly decreased the catalyst leaching into the organic layer upon extraction of the product. Eventually, the optimized microemulsion system could be applied to a wide range of aromatic ketones that were reduced with good isolated yields (up to 98%) and enantioselectivities (up to 97%), while aliphatic ketones were less successful. In the experiment, the researchers used many compounds, for example, 1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7Electric Literature of C15H13N).

1-Phenyl-3,4-dihydroisoquinoline (cas: 52250-50-7) belongs to isoquinoline derivatives. Being an analog of pyridine, isoquinoline is a weak base, with a pKa of 5.14. Most traditional methods of generating isoquinoline do so via oxidative aromatization of dihydro- or tetrahydro-isoquinolines, usually offering some environmental or economic advantage.Electric Literature of C15H13N

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Synthesis of annulated thiophene perylene bisimide analogues: their applications to bulk heterojunction organic solar cells was written by Choi, Hyunbong;Paek, Sanghyun;Song, Juman;Kim, Chulwoo;Cho, Nara;Ko, Jaejung. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2011.Quality Control of 2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone This article mentions the following:

Annulated thiophene perylene bisimides and their triphenyl-amine based oligomers were synthesized. One of the oligomers FPTTPA was demonstrated to be an efficient electron donor in bulk heterojunction organic solar cells, giving a power conversion efficiency of 1.42%. In the experiment, the researchers used many compounds, for example, 2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone (cas: 110590-84-6Quality Control of 2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone).

2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone (cas: 110590-84-6) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.Quality Control of 2,9-Di(tridecan-7-yl)anthra[2,1,9-def:6,5,10-d’e’f’]diisoquinoline-1,3,8,10(2H,9H)-tetraone

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Berberine suppresses colorectal cancer by regulation of Hedgehog signaling pathway activity and gut microbiota was written by Sun, Qiang;Yang, Han;Liu, Maolun;Ren, Shan;Zhao, Hui;Ming, Tianqi;Tang, Shun;Tao, Qiu;Chen, Li;Zeng, Sha;Duan, Dayue Darrel;Xu, Haibo. And the article was included in Phytomedicine in 2022.Electric Literature of C20H18NO4 This article mentions the following:

A growing body of evidence reveals that dysregulation of Hedgehog signaling pathway and dysbiosis of gut microbiota are associated with the pathogenesis of colorectal cancer (CRC). Berberine, a botanical benzylisoquinoline alkaloid, possesses powerful activities against various malignancies including CRC, with the underlying mechanisms to be illuminated. The present study investigated the potencies of berberine on CRC and deciphered the action mechanisms in the context of Hedgehog signaling cascade and gut microbiota. The effects of berberine on the malignant phenotype, apoptosis, cell cycle and Hedgehog signaling of CRC cells were examined in vitro. In azoxymethane/dextran sulfate sodium-caused mouse CRC, the efficacies of berberine on the carcinogenesis, pathol. profile, apoptosis, cell cycle and Hedgehog signaling were determined in vivo. Also, the influences of berberine on gut microbiota in CRC mice were assessed by high-throughput DNA sequencing anal. of 16S rRNA of fecal microbiome in CRC mice. In the present study, berberine was found to dampen the proliferation, migration, invasion and colony formation of CRC cells, without toxicity to normal colonic cells. Addnl., berberine induced apoptosis and arrested cell cycle at G0/G1 phase in CRC cells, accompanied by reduced Hedgehog signaling pathway activity in vitro. In mouse CRC, berberine suppressed tumor growth, ameliorated pathol. manifestations, and potentially induced the apoptosis and cell cycle arrest of CRC, with lowered Hedgehog signaling cascade in vivo. Addnl., berberine decreased 尾-diversity of gut microbiota in CRC mice, without influence on 伪-diversity. Berberine also enriched probiotic microbes and depleted pathogenic microbes, and modulated the functionality of gut microbiota in CRC mice. Overall, berberine may suppress colorectal cancer, orchestrated by down-regulation of Hedgehog signaling pathway activity and modulation of gut microbiota. In the experiment, the researchers used many compounds, for example, 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium (cas: 2086-83-1Electric Literature of C20H18NO4).

9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium (cas: 2086-83-1) belongs to isoquinoline derivatives. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.Electric Literature of C20H18NO4

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Selective Ortho Methylation of Nitroheteroaryls by Vicarious Nucleophilic Substitution was written by Achmatowicz, Michal;Thiel, Oliver R.;Gorins, Gilles;Goldstein, Corinne;Affouard, Caroline;Jensen, Randy;Larsen, Robert D.. And the article was included in Journal of Organic Chemistry in 2008.Related Products of 188121-31-5 This article mentions the following:

An efficient and scalable three-step one-pot approach to 6-methyl-5-nitroisoquinoline from inexpensive 5-nitroisoquinoline, utilizing the vicarious nucleophilic substitution (VNS) as a key step, is described. The optimized reaction conditions can be applied to a limited number of other aromatic and heteroaromatic nitro compounds Attempts to understand the observed selectivity in the VNS step led to the discovery of two new reaction pathways under VNS conditions, one leading to an isoxazole and the other resulting in the formal cyclopropanation of an aromatic nitro compound In the experiment, the researchers used many compounds, for example, 6-Methyl-5-nitroisoquinoline (cas: 188121-31-5Related Products of 188121-31-5).

6-Methyl-5-nitroisoquinoline (cas: 188121-31-5) belongs to isoquinoline derivatives. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.Related Products of 188121-31-5

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The role of pregabalin in relieving ureteral stent-related symptoms: a randomized controlled clinical trial was written by Ragab, Maged;Soliman, Mohamed G.;Tawfik, Ahmed;Abdel Raheem, Ali;El-Tatawy, Hassan;Abo Farha, Mohamed;Magdy, Michael;Elashry, Osama. And the article was included in International Urology and Nephrology in 2017.Formula: C23H26N2O2 This article mentions the following:

Purpose: To investigate the role of pregabalin in relieving USRS in patients with an indwelling double-J (DJ) stents. Patients and methods: A total of 500 adult patients with a unilateral single ureteral stone who underwent ureteroscopic stone management and required DJ stent insertion were prospectively included in our study. Patients were blindly assigned into four groups A, B, C and D. Those in group A were managed with combination of solifenacin 5-mg tablets and pregabalin 75-mg capsules bid. Patients in group B were managed with solifenacin 5-mg tablets. Those in group C were managed with pregabalin 75-mg capsules bid. Those in group D were control group. All patients were evaluated on day 15 postoperatively for stent-related symptoms using the Arabic translated and validated ureteral stent symptom questionnaire (USSQ). Results: The total USSQ score as well as general health index was significantly lower in group A as compared to other groups. In addition, urinary symptom index was significantly improved in both groups A and B as compared to group C and group D. Pain symptom index was significantly improved in both groups A and C as compared to groups B and D. No statistically significant difference was reported regarding sexual index and work performance index among the whole study groups. Conclusion: Pregabalin appears to be a well-tolerated, safe and effective drug in reducing most of USRS, especially relief of pain with subsequent improvement of patient’s quality of life. Its combination with solifenacin should be considered to manage patients with USRS as it shows a significant improvement in total USSQ score and general health index when compared to each drug alone. In the experiment, the researchers used many compounds, for example, (S)-(R)-Quinuclidin-3-yl 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (cas: 242478-37-1Formula: C23H26N2O2).

(S)-(R)-Quinuclidin-3-yl 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (cas: 242478-37-1) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. They are also used to make oil-soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. Formula: C23H26N2O2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Fasudil hydrochloride hydrate, a Rho-kinase inhibitor, suppresses high glucose-induced proliferation and collagen synthesis in rat cardiac fibroblasts was written by Zhou, Hong;Zhang, Kai-Xia;Li, Yong-Jun;Guo, Bing-Yan;Wang, Mei;Wang, Mian. And the article was included in Clinical and Experimental Pharmacology and Physiology in 2011.Electric Literature of C14H18ClN3O2S This article mentions the following:

Hyperglycemia promotes the proliferation of cardiac fibroblasts (CFs) and collagen synthesis in CFs. The objectives of the present study were to determine the effects of fasudil hydrochloride hydrate, a Rho-kinase (ROCK) inhibitor, on high glucose (HG)-induced proliferation of CFs and collagen production in rat CFs and to investigate the mol. mechanism of action of fasudil. Rat CFs were cultured in Dulbecco’s modified Eagle’s medium, supplemented with 5.5 or 25 mmol/L D-glucose or 5.5 mmol/L D-glucose + 19.5 mmol/L mannose, in the presence of absence of fasudil (50 or 100 渭mol/L). Proliferation was measured by the 3-(4,5-dimethyl-2 thiazoyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, whereas the production of type I collagen was evaluated using ELISA and the expression of ROCK1, c-Jun N-terminal kinase (JNK) and type I procollagen mRNA was determined by reverse transcription-polymerase chain reaction. Intracellular type I procollagen protein levels were evaluated using immunocytochem. Western blot anal. was used to evaluate the phosphorylation of myosin phosphatase target subunit 1 (MYPT1), JNK and Smad2/3, as well as c-jun protein levels. Both concentrations of fasudil effectively inhibited HG (25 mmol/L D-glucose)-induced increases in the proliferation of CFs and collagen synthesis, concomitant with suppression of HG-induced upregulation of ROCK1 and JNK mRNA expression and c-jun protein levels, as well as the phosphorylation of MYPT1, JNK and Smad2/3. These data suggest that ROCK activation is essential for the proliferation of CFs and collagen synthesis induced by HG. Fasudil suppressed HG-induced increases in the proliferation of CFs and collagen synthesis, which may be associated with inhibition of the JNK and transforming growth factor 尾/Smad pathways. The results of the present study indicate that inhibition of ROCK may be a novel therapeutic target for the prevention of diabetic cardiac fibrosis. In the experiment, the researchers used many compounds, for example, 5-((1,4-Diazepan-1-yl)sulfonyl)isoquinoline hydrochloride (cas: 105628-07-7Electric Literature of C14H18ClN3O2S).

5-((1,4-Diazepan-1-yl)sulfonyl)isoquinoline hydrochloride (cas: 105628-07-7) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. Other industrial applications include their use as corrosion inhibitors, preservatives, and as solvents for resins and terpenes.Electric Literature of C14H18ClN3O2S

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Efficient and one-pot synthesis of novel sulfamates from carboxylic acids was written by Atmaca, Ufuk. And the article was included in Tetrahedron in 2019.Name: Isoquinoline-1-carboxylic acid This article mentions the following:

Novel sulfamates RC(O)NHSO₃Me [R = cyclohexyl, Ph, H₅C₆CH₂CH₂, etc.] from carboxylic acids and methanol in the presence of chlorosulfonyl isocyanate in mild conditions were synthesized. Several acids, bases and solvents effects were investigated for one-pot synthesis of sulfamates as a catalyst. Finally, triflic acid was found to possess efficiently under optimized conditions in acetonitrile. This method was easy to handle, without any metal, environmentally benign and with short reaction time. Sulfamates could be synthesized on grams and milligrams scale. In the experiment, the researchers used many compounds, for example, Isoquinoline-1-carboxylic acid (cas: 486-73-7Name: Isoquinoline-1-carboxylic acid).

Isoquinoline-1-carboxylic acid (cas: 486-73-7) 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鈥揊ritsch 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.Name: Isoquinoline-1-carboxylic acid

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem