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2-(Benzyloxy)-3-methoxybenzaldehyde, also known as benzyl-o-vanillin, is an off-white to light yellow crystalline powder that can be synthesized from the reaction of o-vanillin with benzyl bromide in acetone, using K2CO3 as a base and tetra-n-butylammonium iodide as a catalyst. 2-(BENZYLOXY)-3-METHOXYBENZALDEHYDE features a dihedral angle of 23.33 (6)° between its two benzene rings and exhibits significant C-HO interactions. It has been recognized as a key reagent in the synthesis of new anticancer drugs and serves as an important pharmacophore in drug discovery, demonstrating anti-proliferative activity in HL60 leukemia cancer cells.

2011-06-5

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2011-06-5 Usage

Uses

Used in Pharmaceutical Industry:
2-(Benzyloxy)-3-methoxybenzaldehyde is used as a key reagent for the synthesis of new anticancer drugs due to its significant anti-proliferative activity in HL60 leukemia cancer cells. Its unique chemical structure and properties make it a promising candidate for the development of novel therapeutic agents.
Used in Drug Discovery:
As an important pharmacophore, 2-(Benzyloxy)-3-methoxybenzaldehyde is utilized in drug discovery to identify and develop new compounds with potential therapeutic applications, particularly in the field of oncology.
Used in Chemical Research:
The compound's unique crystal structure and C-HO interactions make it an interesting subject for chemical research, where it can be studied to understand its properties and potential applications in various chemical and material science fields.

Check Digit Verification of cas no

The CAS Registry Mumber 2011-06-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,1 and 1 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2011-06:
(6*2)+(5*0)+(4*1)+(3*1)+(2*0)+(1*6)=25
25 % 10 = 5
So 2011-06-5 is a valid CAS Registry Number.
InChI:InChI=1/C15H14O3/c1-17-14-9-5-8-13(10-16)15(14)18-11-12-6-3-2-4-7-12/h2-10H,11H2,1H3

2011-06-5Relevant academic research and scientific papers

Synthesis and structure–activity relationships of aristoyagonine derivatives as brd4 bromodomain inhibitors with x-ray co-crystal research

Jung, Kwan-Young,Kim, Yeongrin,Lee, Byung Il,Lee, Joo-Youn,Lee, Kyu Myung,Park, Chi Hoon,Park, Tae Hyun,Ryu, Seong Eon,Yoo, Minjin,Yoo, Miyoun

, (2021/06/16)

Epigenetic regulation is known to play a key role in progression of anti-cancer therapeutics. Lysine acetylation is an important mechanism in controlling gene expression. There has been increasing interest in bromodomain owing to its ability to modulate t

ANGIOTENSIN II RECEPTOR 2 ANTAGONIST SALT FORM AND CRYSTALLINE FORM, AND PREPARATION METHOD THEREFOR

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Paragraph 0109-0110; 0118-0120, (2021/07/10)

Disclosed are an angiotensin II receptor 2 (AT2R) antagonist salt form and crystalline form, a preparation method therefor, and an application of the salt form and crystalline form in preparing a drug which treats chronic pain.

CARBOXYLIC ACID DERIVATIVE AS AT2R RECEPTOR ANTAGONIST

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Paragraph 0116; 0117, (2020/03/24)

The present invention relates to a compound shown in formula (II) or a pharmaceutically acceptable salt thereof and an application of the same in preparing a drug for treating a disease related to angiotensin II receptor type 2 (AT2R).(II)

New hybrid pyrazole and imidazopyrazole antinflammatory agents able to reduce ROS production in different biological targets

Brullo, Chiara,Massa, Matteo,Rapetti, Federica,Alfei, Silvana,Bertolotto, Maria B.,Montecucco, Fabrizio,Signorello, Maria Grazia,Bruno, Olga

, (2020/02/22)

Several anti-inflammatory agents based on pyrazole and imidazopyrazole scaffolds and a large library of substituted catechol PDE4D inhibitors were reported by us in the recent past. To obtain new molecules potentially able to act on different targets involved in inflammation onset we designed and synthesized a series of hybrid compounds by linking pyrazole and imidazo-pyrazole scaffolds to differently decorated catechol moieties through an acylhydrazone chain. Some compounds showed antioxidant activity, inhibiting reactive oxygen species (ROS) elevation in neutrophils, and a good inhibition of phosphodiesterases type 4D and, particularly, type 4B, the isoform most involved in inflammation. In addition, most compounds inhibited ROS production also in platelets, confirming their ability to exert an antiinflammatory response by two independent mechanism. Structure–activity relationship (SAR) analyses evidenced that both heterocyclic scaffolds (pyrazole and imidazopyrazole) and the substituted catechol moiety were determinant for the pharmacodynamic properties, even if hybrid molecules bearing to the pyrazole series were more active than the imidazopyrazole ones. In addition, the pivotal role of the catechol substituents has been analyzed. In conclusion the hybridization approach gave a new serie of multitarget antiinflammatory compounds, characterized by a strong antioxidant activity in different biological targets.

Preparation technology of 1-(2-hydroxy-3-methoxyphenyl)ethanone

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Paragraph 0016-0038; 0046-0068; 0076-0088, (2017/08/27)

The invention discloses a preparation technology of 1-(2-hydroxy-3-methoxyphenyl)ethanone. Through protecting group addition, alkylation, oxidation and deprotection, 1-(2-hydroxy-3-methoxyphenyl)ethanone is prepared from o-vanillin as a raw material. The

Benzo aza compound, preparation method and use thereof

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Paragraph 0099; 0100, (2017/08/22)

Belonging to the field of pharmaceutical chemistry, the invention relates to a benzoazepine compound, a preparation method and application thereof, in particular to the benzoazepine compound, its preparation method and application in the field of treatment of nervous system diseases, especially application in the field of drug addiction related to dopamine D1 and D3 receptors. The benzoazepine compound and pharmacologically acceptable inorganic or organic salts thereof have a structure shown as formula (I). Results of drug experiments carried out by the invention show that the benzoazepine compound and its pharmacologically acceptable inorganic or organic salts have high antagonistic activity on dopamine D1 and D3, can be used as drug leads for further development of dopamine receptor antagonists with good selectivity and high activity, and can be used as potential drugs for treatment of drug addiction by dopamine D1, D3 receptor antagonists. (formula (I)).

Hydride transfer reactions of 5-(2-alkohybenzylidene) barbituric acids: Synthesis of 2,4,6-trioxoperhydropyrimidine-5-spiro-3′-chromanes

Krasnov, Konstantin A.,Dorovatovskii, Pavel V.,Zubavichus, Yan V.,Timofeeva, Tatiana V.,Khrustalev, Victor N.

, p. 542 - 549 (2017/01/12)

The thermal cyclization of 5-(2-phenoxymethylphenyl-methylene)barbituric acid and its derivatives affords 2,4,6-trioxoperhydropyrimidine-5-spiro-3′-chromanes. The reactions require no catalysts and proceed at temperatures from 118 to 240?°C depending on the substrate activity. These cyclization reactions are analogous to T-reactions of tertiary amines involving the hydride transfer.

Functional reversal of (?)-Stepholidine analogues by replacement of benzazepine substructure using the ring-expansion strategy

Li, Wei,Zhang, Li,Xu, Lili,Yuan, Congmin,Du, Peng,Chen, Jiaojiao,Zhen, Xuechu,Fu, Wei

, p. 599 - 607 (2016/10/06)

(?)-Stepholidine is an active ingredient of the Chinese herb Stephania and naturally occurring tetrahydroprotoberberine alkaloid with mixed dopamine receptor D1 agonistic and dopamine receptor D2 antagonistic activities. In this work, a series of novel hexahydrobenzo[4,5]azepino [2,1-a]isoquinolines were designed and synthesized as ring-expanded analogues of (?)-Stepholidine. Initial pharmacological assays demonstrated that a benzazepine replacement was associated with significant increase in selectivity and functional reversal at dopamine receptor D1. Compound-(?)-15e (Ki?=?5.32?±?0.01?nm) is more potent than (?)-Stepholidine (Ki?=?13?nm) and was identified as a selective dopamine receptor D1 antagonist (IC50?=?0.14?μm). Moreover, molecular modeling suggested that (?)-15e might exert its dopamine receptor D1 antagonistic activities through interacting with the transmembrane helix 7 of dopamine receptor D1.

Synthesis of enantiopure angiotensin II type 2 receptor [AT2R] antagonist EMA401

Wakchaure, Prasad B.,Bremberg, Ulf,Wannberg, Johan,Larhed, Mats

, p. 6881 - 6887 (2015/08/24)

We report a facile synthesis of the angiotensin II type 2 receptor antagonist EMA401, which recently passed phase II clinical trials, in high overall yield. The synthesis of the key phenylalanine intermediate involved the formation of an α-nitro cinnamic ester and its reduction followed by a Pictet-Spengler cyclization, which furnished the tetrahydroisoquinoline core structure. Next, EMA401 was separated from its enantiomer EMA402 by four recrystalizations of a diastereomeric salt in 98% ee. All steps were performed on gram scale with emphasis on avoiding column purification and using readily available low cost starting materials and reagents.

HETEROCYCLIC COMPOUNDS AND METHODS OF THEIR USE

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Page/Page column 43, (2015/02/02)

The present invention relates generally to compounds that are useful in antagonizing the angiotensin II type 2 (AT2) receptor. More particularly, the invention relates to substituted isoquinoline compounds and their use as AT2 receptor antagonists. Pharmaceutical compositions comprising the compounds and their use in modulating the AT2 receptor and therapies that require modulation of the AT2 receptor are described.

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