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2-ETHOXY-6,9-DIAMINOACRIDINE is a chemical compound belonging to the acridine family, characterized by the presence of an ethoxy group at the 2nd position and two amino groups at the 6th and 9th positions. It exhibits unique chemical and biological properties, making it a potential candidate for various applications in different fields.

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  • 442-16-0 Structure
  • Basic information

    1. Product Name: 2-ETHOXY-6,9-DIAMINOACRIDINE
    2. Synonyms: 2-ETHOXY-6,9-DIAMINOACRIDINE;6,9-DIAMINO-2-ETHOXYACRIDINE;7-ETHOXY-ACRIDINE-3,9-DIAMINE;ACRINOL;RIVANOL;Ethacridine;Ethacrindine;6,9-DIAMINO-2-ETHOXYACRIDINEHYDROCHLORIDE
    3. CAS NO:442-16-0
    4. Molecular Formula: C15H15N3O
    5. Molecular Weight: 253.3
    6. EINECS: 207-130-9
    7. Product Categories: N/A
    8. Mol File: 442-16-0.mol
  • Chemical Properties

    1. Melting Point: 226°
    2. Boiling Point: 396.5°C (rough estimate)
    3. Flash Point: 270.4 °C
    4. Appearance: /
    5. Density: 1.0966 (rough estimate)
    6. Refractive Index: 1.5700 (estimate)
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. PKA: 11.22±0.10(Predicted)
    10. CAS DataBase Reference: 2-ETHOXY-6,9-DIAMINOACRIDINE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2-ETHOXY-6,9-DIAMINOACRIDINE(442-16-0)
    12. EPA Substance Registry System: 2-ETHOXY-6,9-DIAMINOACRIDINE(442-16-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 442-16-0(Hazardous Substances Data)

442-16-0 Usage

Uses

Used in Pharmaceutical Industry:
2-ETHOXY-6,9-DIAMINOACRIDINE is used as a pharmaceutical agent for cancer treatment. It has been found to induce a regeneration-like response in biological studies, which contributes to cancer regression. 2-ETHOXY-6,9-DIAMINOACRIDINE activates the expression and/or function of YAP and/or TAZ, key proteins involved in cell proliferation, survival, and tissue regeneration.
Used in Research Applications:
In addition to its pharmaceutical applications, 2-ETHOXY-6,9-DIAMINOACRIDINE is also utilized in research settings for studying the molecular mechanisms underlying cancer progression and regression. Its ability to modulate the expression and function of YAP and TAZ makes it a valuable tool for investigating the role of these proteins in cancer biology and potential therapeutic targets.

Purification Methods

It crystallises from 50% EtOH or EtOH as orange-yellow crystals. It also crystallises as a monohydrate m 116-118o. It has a pK2 0 of 11.04 in 50% aqueous EtOH. The methiodide is soluble in H2O and has m 332-334o (dec) (from aqueous Me2CO). [Albert & Gledhill J Soc Chem Ind 61 159 1942, Foye et al. J Pharm Sci 57 1795 1968, Albert & Goldacre J Chem Soc 708 1946, Beilstein 22 II 458, 22 III/IV 6679, 22/12 V 243.]

Check Digit Verification of cas no

The CAS Registry Mumber 442-16-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,4 and 2 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 442-16:
(5*4)+(4*4)+(3*2)+(2*1)+(1*6)=50
50 % 10 = 0
So 442-16-0 is a valid CAS Registry Number.
InChI:InChI=1/C15H15N3O/c1-2-19-10-4-6-13-12(8-10)15(17)11-5-3-9(16)7-14(11)18-13/h3-8H,2,16H2,1H3,(H2,17,18)

442-16-0Relevant articles and documents

Development of WNK signaling inhibitors as a new class of antihypertensive drugs

Ishigami-Yuasa, Mari,Watanabe, Yuko,Mori, Takayasu,Masuno, Hiroyuki,Fujii, Shinya,Kikuchi, Eriko,Uchida, Shinichi,Kagechika, Hiroyuki

, p. 3845 - 3852 (2017/06/13)

Pseudohypoaldosteronism type II (PHAII) is characterized by hyperkalemia and hypertension despite a normal glomerular filtration rate. Abnormal activation of the signal cascade of with-no-lysine kinase (WNK) with OSR1 (oxidative stress-responsive kinase 1)/SPAK (STE20/SPS1-related proline/alanine-rich kinase) and NCC (NaCl cotransporter) results in characteristic salt-sensitive hypertension. Thus, inhibitors of the WNK-OSR1/SPAK-NCC cascade are candidates for a new class of antihypertensive drugs. In this study, we developed novel inhibitors of this signal cascade from the 9-aminoacridine lead compound 1, one of the hit compounds obtained by screening our chemical library for WNK-SPAK binding inhibitors. Among the synthesized acridine derivatives, several acridine-3-amide and 3-urea derivatives, such as 10 (IC50: 6.9?μM), 13 (IC50: 2.6?μM), and 20 (IC50: 4.8?μM), showed more potent inhibitory activity than the lead compound 1 (IC50: 15.4?μM). Compounds 10 and 20 were confirmed to inhibit phosphorylation of NCC in vivo.

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