SP2509

Base Information

• Chemical Name: SP2509
• CAS No.: 1423715-09-6
• Molecular Formula: C19H20ClN3O5S
• Molecular Weight: 437.904
• Mol file: 1423715-09-6.mol

Synonyms:SP2509;(E)-N'-(1-(5-chloro-2-hydroxyphenyl)ethylidene)-3-(morpholinosulfonyl)benzohydrazide;HCI-2509;(E)-N'-(1-(5-chloro-2-hydroxyphenyl)ethylidene)-3-(morpholinosulfonyl)benzohydrazide SP2509;3-(4-Morpholinylsulfonyl)benzoic acid (2E)-2-[1-(5-chloro-2-hydroxyphenyl)ethylidene]hydrazide

Chemical Property of SP2509

Chemical Property:

• PSA: 116.68000
• LogP: 3.63010
• Storage Temp.: +2C to +8C
• Solubility.: Soluble in DMSO (up to at least 25 mg/ml)

Purity/Quality:

99% ^*data from raw suppliers

SP-2509 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: SP2509 (1423715-09-6) is a potent (IC50 = 13 nM) and reversible inhibitor of the histone demethylase LSD1 (KDM1A).1 It is inactive against the closely related flavin enzymes MAO A,B as well as lactate dehydrogenase, several CYP’s and hERG. LSD1 regulates the balance between self-renewal and differentiation of stem cells and is highly expressed in various cancers.2-6 SP2509 promotes autophagy in neuroblastoma cells.7
• Uses: SP 2509 reduces the effect of the LSD1 binding to CoREST, resulting in increased methylation of H3K4 and driving increased expression of p21, p27 and CCAAT/enhancer binding protein α in acute myeloid leukemia cells. Anti-leukemia agent.

Technology Process of SP2509

There total 4 articles about SP2509 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: 85.0%

3-(morpholinosulfonyl)benzohydrazide + 5-chloro-2-hydroxyacetophenone (1450-74-4) → ((E)-N’-(1-(5-chloro-2-hydroxyphenyl)ethylidene)-3-(morpholinosulfonyl)benzohydrazide) (1423715-09-6)

Guidance literature:

With acetic acid; In methanol; at 120 ℃; for 0.5h; Microwave irradiation;

DOI:10.1021/jm400870h

Reference yield:

3-Carboxybenzenesulfonyl chloride (4025-64-3) → ((E)-N’-(1-(5-chloro-2-hydroxyphenyl)ethylidene)-3-(morpholinosulfonyl)benzohydrazide) (1423715-09-6)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / tetrahydrofuran / 1 h / 20 °C

2: sulfuric acid / 65 °C

3: hydrazine hydrate / methanol / 12 h / 65 °C

4: acetic acid / methanol / 0.5 h / 120 °C / Microwave irradiation

With sulfuric acid; potassium carbonate; hydrazine hydrate; acetic acid; In tetrahydrofuran; methanol;

DOI:10.1021/jm400870h

Reference yield:

methyl 3-(morpholinosulfonyl)benzoate (412940-98-8) → ((E)-N’-(1-(5-chloro-2-hydroxyphenyl)ethylidene)-3-(morpholinosulfonyl)benzohydrazide) (1423715-09-6)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine hydrate / methanol / 12 h / 65 °C

2: acetic acid / methanol / 0.5 h / 120 °C / Microwave irradiation

With hydrazine hydrate; acetic acid; In methanol;

DOI:10.1021/jm400870h

upstream raw materials:

5-chloro-2-hydroxyacetophenone

3-Carboxybenzenesulfonyl chloride

3-(morpholin-4-ylsulfonyl) benzoic acid

methyl 3-(morpholinosulfonyl)benzoate

Refernces

• 1、 -. "SUBSTITUTED (E)-N'-(1-PHENYLETHYLIDENE) BENZOHYDRAZIDE ANALOGS AS HISTONE DEMETHYLASE INHIITORS". Page/Page column 86; 87. . Retrieved 2013/03/26.