Sematilide

{{chembox

| Verifiedfields = changed

| verifiedrevid = 464389005

| ImageFile=Sematilide.png

| ImageClass = skin-invert-image

| ImageSize=200px

| PIN=N-[2-(Diethylamino)ethyl]-4-(methanesulfonamido)benzamide

| OtherNames=

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 0NHB13IN3R

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII1 = 1B8MC21ZI2

| UNII1_Comment = (HCl)

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 52715

| InChI = 1/C14H23N3O3S/c1-4-17(5-2)11-10-15-14(18)12-6-8-13(9-7-12)16-21(3,19)20/h6-9,16H,4-5,10-11H2,1-3H3,(H,15,18)

| InChIKey = KHYPYQZQJSBPIX-UHFFFAOYAU

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 95804

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C14H23N3O3S/c1-4-17(5-2)11-10-15-14(18)12-6-8-13(9-7-12)16-21(3,19)20/h6-9,16H,4-5,10-11H2,1-3H3,(H,15,18)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KHYPYQZQJSBPIX-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=101526-83-4

| CASNo1_Ref = {{cascite|correct|CAS}}

| CASNo1 = 101526-62-9

| CASNo1_Comment =(HCl)

| PubChem=58505

| SMILES = O=S(=O)(Nc1ccc(cc1)C(=O)NCCN(CC)CC)C

| MeSHName=Sematilide

}}

|Section2={{Chembox Properties

| Formula=C14H23N3O3S

| MolarMass=313.42 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

Sematilide is an antiarrhythmic agent. It is the same structure as for procainamide, differing only by the placement of a mesyl sulfonamide moiety to the anilino nitrogen.

Synthesis

File:Sematilide synthesis.svg

Sematilide can be synthesized from benzocaine (1).{{cite journal | doi = 10.1021/jm00388a001 | title = Rational design of 4-[(methylsulfonyl)amino]benzamides as class III antiarrhythmic agents | date = 1987 | last1 = Lumma | first1 = William C. | last2 = Wohl | first2 = Ronald A. | last3 = Davey | first3 = David D. | last4 = Argentieri | first4 = Thomas M. | last5 = Devita | first5 = Robert J. | last6 = Gomez | first6 = Robert P. | last7 = Jain | first7 = Vijay K. | last8 = Marisca | first8 = Anthony J. | last9 = Morgan | first9 = Thomas K. | last10 = Reiser | first10 = H. J. | journal = Journal of Medicinal Chemistry | volume = 30 | issue = 5 | pages = 755–758 | pmid = 3572962 }}David D. Davey, William C. Lumma, Jr., Ronald A. Wohl, {{US patent|4544654}} (1985 to Schering A.G.) Reaction with mesyl chloride, followed by saponification and removal of the water from the reaction mixture, gives sodium 4-[(methylsulfonyl)amino]benzoate (2). Chlorination with thionyl chloride gives 4-[(methylsulfonyl)amino]benzoyl chloride. Amide formation with N,N-diethylethylenediamine (3) then concludes the synthesis of sematilide (4).

References