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METHYL 5-AMINOSALICYLATE, also known as 5-Amino-2-hydroxybenzoic Acid Methyl Ester, is a disubstituted benzoic acid derivative with significant potential in the pharmaceutical industry. It is characterized by its unique chemical structure, which allows it to be utilized in the development of various pharmaceutical compounds.

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  • 42753-75-3 Structure
  • Basic information

    1. Product Name: METHYL 5-AMINOSALICYLATE
    2. Synonyms: 5-amino-2-hydroxy-benzoicacimethylester;5-aminomethylsalicylicacid;5-amino-salicylicacimethylester;METHYL 5-AMINOSALICYLATE;METHYL 5-AMINO-2-HYDROXYBENZOATE;5-AMINO-2-HYDROXYBENZOIC ACID METHYL ESTER;5-AMINO SALICYLIC ACID METHYL ESTER;5-Aminomethylsalicylate
    3. CAS NO:42753-75-3
    4. Molecular Formula: C8H9NO3
    5. Molecular Weight: 167.16
    6. EINECS: N/A
    7. Product Categories: Aromatic Esters;pharmacetical;C8 to C9;Carbonyl Compounds;Esters;amine|alcohol|carboxylic ester
    8. Mol File: 42753-75-3.mol
  • Chemical Properties

    1. Melting Point: 95-99 °C(lit.)
    2. Boiling Point: 319.2°Cat760mmHg
    3. Flash Point: 146.8°C
    4. Appearance: /
    5. Density: 1.305g/cm3
    6. Vapor Pressure: 0.000184mmHg at 25°C
    7. Refractive Index: 1.605
    8. Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
    9. Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
    10. PKA: 10.02±0.18(Predicted)
    11. CAS DataBase Reference: METHYL 5-AMINOSALICYLATE(CAS DataBase Reference)
    12. NIST Chemistry Reference: METHYL 5-AMINOSALICYLATE(42753-75-3)
    13. EPA Substance Registry System: METHYL 5-AMINOSALICYLATE(42753-75-3)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 22-36/37/38-43
    3. Safety Statements: 26
    4. WGK Germany: 2
    5. RTECS: VO1683100
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 42753-75-3(Hazardous Substances Data)

42753-75-3 Usage

Uses

Used in Pharmaceutical Industry:
METHYL 5-AMINOSALICYLATE is used as a key intermediate compound for the synthesis of various pharmaceutical compounds, particularly sphingosine kinase inhibitors. These inhibitors play a crucial role in the treatment of various diseases, including cancer, inflammatory disorders, and neurodegenerative conditions, by targeting the sphingosine kinase enzyme and modulating its activity.
In the development of sphingosine kinase inhibitors, METHYL 5-AMINOSALICYLATE serves as a building block, providing the necessary structural framework for the design and synthesis of potent and selective inhibitors. These inhibitors can potentially be used in the treatment of a wide range of diseases by modulating the sphingolipid signaling pathway, which is often dysregulated in various pathological conditions.
Furthermore, METHYL 5-AMINOSALICYLATE may also find applications in other areas of the pharmaceutical industry, such as the development of novel drugs targeting different enzymes or receptors, or as a component in the synthesis of complex drug molecules with multiple therapeutic targets.

Check Digit Verification of cas no

The CAS Registry Mumber 42753-75-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,2,7,5 and 3 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 42753-75:
(7*4)+(6*2)+(5*7)+(4*5)+(3*3)+(2*7)+(1*5)=123
123 % 10 = 3
So 42753-75-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO3/c1-12-8(11)6-4-5(9)2-3-7(6)10/h2-4,10H,9H2,1H3

42753-75-3Relevant articles and documents

Inhibition of 3D colon cancer stem cell spheroids by cytotoxic RuII-p-cymene complexes of mesalazine derivatives

Acharya, Sourav,Ghosh, Subhashis,Maji, Moumita,Mukherjee, Arindam,Parambil, Ajmal Roshan Unniram,Singh, Sandeep

, p. 5421 - 5424 (2020)

The Ru(ii) complex of an imidazole-mesalazine Schiff base is a unique example showing growth inhibition of 3D-colon cancer stem cell spheroids and bulk colon cancer cells at lower dosage than salinomycin or oxaliplatin. Unlike oxaliplatin which increases

MODIFIED PROTEINS AND PROTEIN DEGRADERS

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Paragraph 00308-00310, (2021/12/08)

Provided herein are compounds, pharmaceutical compositions, and methods for binding or degrading target proteins. Further provided herein are compounds having a DNA damage-binding protein 1 (DDB1) binding moiety. Some such embodiments include a linker. Some such embodiments include a target protein binding moiety. Further provided herein are ligand-DDB1 complexes. Further provided herein are in vivo modified DDB1 proteins.

Synthesis and biological evaluation of salicylic acid analogues of celecoxib as a new class of selective cyclooxygenase-1 inhibitor

Yoon, Sung-Hwa,Cho, Duk-Yeon,Choi, Seoung-Ryoung,Lee, Joo-Young,Choi, Dong-Kug,Kim, Eunha,Park, Ju-Young

, p. 1230 - 1238 (2021/09/06)

A series of salicylic acid analogues of celecoxib where the phenylsulfonamide moiety in the structure of celecoxib is replaced by salicylic acid moiety was synthesized and tested for in vitro cyclooxygenase (COX)-1 and COX-2 enzyme inhibition. Among the series, 5-substituted-2-hydroxy-benzoic acid analogues (7a–7h) generally showed better inhibitory activities on both enzymes than 4-substituted-2-hydroxy-ben-zoic acid analogues (12a–12h). In particular, the chloro analogue 7f which had the highest inhibitory effect (IC50=0.0057μM) to COX-1 with excellent COX-1 selectivity (SI=768) can be classified as a new potent and selective COX-1 inhibitor. The high inhibitory potency of 7f was rationalized through the docking simulation of this analogue in the active site of COX-1 enzyme.

PYROPTOSIS-INDUCED IMMUNOTHERAPY

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Paragraph 041; 074, (2021/03/05)

Pyroptosis-induced immunotherapy is effected by activating a pore-forming, pyrpotogenic molecule, wherein the activating induces tumor cell pryoptosis and causes tumor regression by T-cell mediated anti-tumor immunity.

EIF4E INHIBITORS AND USES THEREOF

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Paragraph 00506; 00520, (2021/09/11)

The present invention provides compounds inhibiting elF4E activity and compositions and methods of using thereof.

A bioorthogonal system reveals antitumour immune function of pyroptosis

Ding, Jingjin,Gao, Wenqing,Huang, Huanwei,Liu, Zhibo,Shao, Feng,Wang, Chunhong,Wang, Qinyang,Wang, Yupeng,Zhou, Xuehan

, (2020/03/16)

Bioorthogonal chemistry capable of operating in live animals is needed to investigate biological processes such as cell death and immunity. Recent studies have identified a gasdermin family of pore-forming proteins that executes inflammasome-dependent and

Carbonyl Sulfide (COS) Donor Induced Protein Persulfidation Protects against Oxidative Stress

Chauhan, Preeti,Gupta, Kavya,Ravikumar, Govindan,Saini, Deepak K.,Chakrapani, Harinath

supporting information, p. 4717 - 4724 (2019/11/03)

The emergence of hydrogen sulfide (H2S) as an important signalling molecule in redox biology with therapeutic potential has triggered interest in generating this molecule within cells. One strategy that has been proposed is to use carbonyl sulfide (COS) as a surrogate for hydrogen sulfide. Small molecules that generate COS have been shown to produce hydrogen sulfide in the presence of carbonic anhydrase, a widely prevalent enzyme. However, other studies have indicated that COS may have biological effects which are distinct from H2S. Thus, it would be useful to develop tools to compare (and contrast) effects of COS and H2S. Here we report enzyme-activated COS donors that are capable of inducing protein persulfidation, which is symptomatic of generation of hydrogen sulfide. The COS donors are also capable of mitigating stress induced by elevated reactive oxygen species. Together, our data suggests that the effects of COS parallel that of hydrogen sulfide, laying the foundation for further development of these donors as possible therapeutic agents.

Synthesis, characterization, and cytotoxic evaluation of some newly substituted diazene candidates

El-Naggar, Mohamed,El-Shorbagi, Abdel-Nasser,Elnaggar, Dina H.,Amr, Abd El-Galil E.,Al-Omar, Mohamed A.,Elsayed, Elsayed A.

, (2019/01/14)

A series of azocompounds containing methyl salicylate 4a-k and 1-naphthyl moiety 6-8 was synthesized and tested as anticancer agents. Nitrosation of methyl 5-amino-2-hydroxybenzoate or 1-aminonaphthalene by using NaNO2 in the presence of HCl af

4-substituted pyridine-2-formamide compound, preparation method thereof and application

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Paragraph 0059-0063, (2018/03/28)

The invention discloses a 4-substituted pyridine-2-formamide compound, a preparation method thereof and an application. The 4-substituted pyridine-2-formamide compound has a structure as shown in a formula I, and the chemical name of the compound is 4-{4-[3-(4-chlorine-3-trifluoromethyl-phenyl)-ureide]-3-carboxyl phenoxy}-N-picoline-2-carboxylic methylamine. According to the preparation method of the 4-substituted pyridine-2-formamide compound, 4-chlorine-2-picolinic acid serves as an initial raw material, and the compound in the formula I is prepared by acylating chlorination, amination, substitution reaction and condensation reaction. The 4-substituted pyridine-2-formamide compound retains a Sorafenib efficacy structure, 5-aminosalicylic acid or aminosalicylic acid ester achieving a positive pharmacological function in the metabolic process replaces p-aminophenol with large toxic and side effects, efficacy can be improved, and the toxic and side effects are reduced.

Calcium Coordination Solids for pH-Triggered Release of Olsalazine

Levine, Dana J.,Gonzalez, Miguel I.,Legendre, Christina M.,Run?evski, Tom?e,Oktawiec, Julia,Colwell, Kristen A.,Long, Jeffrey R.

supporting information, p. 1739 - 1742 (2017/11/15)

Calcium coordination solids were synthesized and evaluated for delivery of olsalazine (H4olz), an anti-inflammatory compound used for treatment of ulcerative colitis. The materials include one-dimensional Ca(H2olz)?4 H2O chains, two-dimensional Ca(H2olz)?2 H2O sheets, and a three-dimensional metal-organic framework Ca(H2olz)?2DMF (DMF=N,N-dimethylformamide). The framework undergoes structural changes in response to solvent, forming a dense Ca(H2olz) phase when exposed to aqueous HCl. The compounds Ca(H2olz)?x H2O (x=0, 2, 4) were each pressed into pellets and exposed to simulated gastrointestinal fluids to mimic the passage of a pill from the acidic stomach to the pH-neutral intestines. All three calcium materials exhibited a delayed release of olsalazine relative to Na2(H2olz), the commercial formulation, illustrating how formulation of a drug within an extended coordination solid can serve to tune its solubility and performance.

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