Pyrrophenone

Base Information

• Chemical Name: Pyrrophenone
• CAS No.: 341973-06-6
• Molecular Formula: C49H37F2N3O5S2
• Molecular Weight: 849.96200
• Mol file: 341973-06-6.mol

Synonyms:

Chemical Property of Pyrrophenone

Chemical Property:

• PSA: 163.25000
• LogP: 9.91570

Purity/Quality:

98%Min ^*data from raw suppliers

Pyrrophenone ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: The group IVA phospholipase A2 (PLA2), known as calcium-dependent cytosolic PLA2 (cPLA2), selectively releases arachidonic acid (AA) from membrane phospholipids, playing a central role in initiating the synthesis of prostaglandins (PGs) and leukotrienes (LTs). Pyrrophenone inhibits cPLA2α with an IC50 of 4.2 nM in enzyme assays and potently blocks the release of AA and the production of PGE2 and LTC4 in cells (IC50 = 24, 25, and 14 nM, respectively). Its action is reversible and selective, as pyrrophenone inhibits the secretory type IB and IIA PLA2s with more than a hundred-fold less potency. Pyrrophenone has also been shown to inhibit calcium ionophore (A23187)-stimulated AA release from monocytic cells, interleukin-1-induced PGE2 synthesis in mesangial cells, and the production of PGE2, LTs, and platelet-activating factor by human neutrophils, always with maximal inhibition at concentrations below 1 μM.

Technology Process of Pyrrophenone

There total 13 articles about Pyrrophenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

phthalic anhydride (85-44-9) → Pyrrophenone (341973-06-6)

Guidance literature:

Multi-step reaction with 4 steps

1: AlCl₃ / 72 h / 20 °C

2: WSC; HOBT / dimethylformamide / 3 h / 20 °C

3: SnCl₂*2H₂O; aq. NaOH / ethanol / 2 h / 0 °C

4: WSC; HOBT / 5 h / 20 °C

With sodium hydroxide; aluminium trichloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; tin(ll) chloride; In ethanol; N,N-dimethyl-formamide; 1: Friedel-Crafts acylation;

DOI:10.1016/S0960-894X(01)00003-8

Reference yield:

1,3-Difluorobenzene (372-18-9) → Pyrrophenone (341973-06-6)

Guidance literature:

Multi-step reaction with 4 steps

1: AlCl₃ / 72 h / 20 °C

2: WSC; HOBT / dimethylformamide / 3 h / 20 °C

3: SnCl₂*2H₂O; aq. NaOH / ethanol / 2 h / 0 °C

4: WSC; HOBT / 5 h / 20 °C

With sodium hydroxide; aluminium trichloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; tin(ll) chloride; In ethanol; N,N-dimethyl-formamide; 1: Friedel-Crafts acylation;

DOI:10.1016/S0960-894X(01)00003-8

Reference yield:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → Pyrrophenone (341973-06-6)

Guidance literature:

Multi-step reaction with 9 steps

1: Et₃N / toluene / 0.33 h / 0 °C

2: NaH / tetrahydrofuran / 2 h / 20 °C

3: LiBH₄ / tetrahydrofuran / 5 h / 20 °C

4: Et₃N / tetrahydrofuran / 1 h / 0 °C

5: NaN₃; HMPA / 2 h / 50 °C

6: HCl / ethyl acetate / 15 h / 0 - 20 °C

7: WSC; HOBT / dimethylformamide / 3 h / 20 °C

8: SnCl₂*2H₂O; aq. NaOH / ethanol / 2 h / 0 °C

9: WSC; HOBT / 5 h / 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium borohydride; sodium azide; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; tin(ll) chloride; In tetrahydrofuran; ethanol; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0960-894X(01)00003-8

upstream raw materials:

4-(2,4-dioxothiazolidin-5-ylidenemethyl)benzoic acid

phthalic anhydride

1,3-Difluorobenzene

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester