13815-71-9

Basic information

• Product Name: Acetaldehyde, (4-methoxyphenyl)hydrazone
• Synonyms: acetaldehyde p-methoxyphenylhydrazone;N-Eth-(E)-ylidene-N'-(4-methoxy-phenyl)-hydrazine;Acetaldehyd-p-methoxy-phenylhydrazon;acetaldehyde 4-methoxyphenylhydrazone;Acetaldehyd-p-methoxyphenylhydrazon;acetaldehyde-p-methoxyphenylhydrazone;ACETALDEHYDE (4-METHOXYPHENYL)HYDRAZONE
• CAS NO: 13815-71-9
• Molecular Formula: C9H12N2O
• Molecular Weight: 164.207
• Mol File: 13815-71-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 122 °C (1 mmHg)
• CAS DataBase Reference: Acetaldehyde, (4-methoxyphenyl)hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: Acetaldehyde, (4-methoxyphenyl)hydrazone(13815-71-9)
• EPA Substance Registry System: Acetaldehyde, (4-methoxyphenyl)hydrazone(13815-71-9)

Safety Data

• Hazardous Substances Data: 13815-71-9(Hazardous Substances Data)

Upstream product

• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 75-07-0 acetaldehyde 
• 3471-32-7 4-Methoxyphenylhydrazine 

Downstream Products

• 23227-36-3 3-[1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-propionic acid 
• 1427215-00-6 4-(1-(4-chlorobenzoyl)-5-methoxy-3-methyl-1H-indol-2-yl)butanoic acid 
• 1427215-15-3 C₂₁H₂₀ClNO₄ 
• 1427215-16-4 2-(1-(4-chlorobenzoyl)-5-methoxy-2-propyl-1H-indol-3-yl)acetic acid 
• 1427215-01-7 C₂₁H₂₀ClNO₄ 
• 1427215-10-8 C₂₇H₂₂ClF₃N₂O₆S 
• 1427215-11-9 C₂₄H₂₀Cl₂N₂O₅S₂ 
• 1427215-12-0 C₂₈H₂₅ClN₂O₆S 
• 1427215-13-1 C₂₉H₂₉ClN₂O₅S 
• 36405-72-8 9-(4-chlorobenzoyl)-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid 
• 1427215-14-2 C₂₂H₂₁ClN₂O₅S 
• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 13815-62-8 N¹-(4-Chlorbenzoyl)-N¹-(4-methoxyphenyl)hydrazin-hydrochlorid 
• 20357-37-3 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride 

Relevant articles and documents

Development of potent and selective indomethacin analogues for the inhibition of AKR1C3 (type 5 17β-hydroxysteroid dehydrogenase/prostaglandin F synthase) in castrate-resistant prostate cancer

Castrate-resistant prostate cancer (CRPC) is a fatal, metastatic form of prostate cancer. CRPC is characterized by reactivation of the androgen axis due to changes in androgen receptor signaling and/or adaptive intratumoral androgen biosynthesis. AKR1C3 is upregulated in CRPC where it catalyzes the formation of potent androgens. This makes AKR1C3 a target for the treatment of CRPC. AKR1C3 inhibitors should not inhibit AKR1C1/AKR1C2, which inactivate 5α-dihydrotestosterone. Indomethacin, used to inhibit cyclooxygenase, also inhibits AKR1C3 and displays selectivity over AKR1C1/AKR1C2. Parallel synthetic strategies were used to generate libraries of indomethacin analogues, which exhibit reduced cyclooxygenase inhibitory activity but retain AKR1C3 inhibitory potency and selectivity. The lead compounds inhibited AKR1C3 with nanomolar potency, displayed >100-fold selectivity over AKR1C1/AKR1C2, and blocked testosterone formation in LNCaP-AKR1C3 cells. The AKR1C3·NADP +·2′-des-methyl-indomethacin crystal structure was determined, and it revealed a unique inhibitor binding mode. The compounds reported are promising agents for the development of therapeutics for CRPC.

Comparative metabolic studies on [14C]-labelled acemetacin and indometacin in rats (author's transl)

1. [14C]-Indometacin and [14C]-Acemetacin are synthesized starting from carboxyl-[14C]-levulinic acid. 2. Renal, biliary and fecal elimination of both compounds occurs mainly within 24 h after intravenous or intraduodenal application to rats and after deg