Chlorotonil A information

Chlorotonil A
Names
	IUPAC name (1S,2R,3Z,5E,7S,10S,14R,15R,16S,20S)-12,12-dichloro-2,7,10,16,18-pentamethyl-8-oxatricyclo[12.8.0.015,20]docosa-3,5,17,21-tetraene-9,11,13-trione
Identifiers
CAS Number	1009813-26-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL4290170;
ChemSpider	28284718;
PubChem CID	24742044;
CompTox Dashboard (EPA)	DTXSID401043833 ;
	InChI InChI=1S/C26H32Cl2O4/c1-14-12-16(3)21-19(13-14)10-11-20-15(2)8-6-7-9-17(4)32-25(31)18(5)23(29)26(27,28)24(30)22(20)21/h6-12,15-22H,13H2,1-5H3/b8-6-,9-7+/t15-,16-,17+,18+,19-,20+,21-,22-/m1/s1 Key: RQYZFUUTQJMTMJ-JCSZEPHKSA-N;
	SMILES C[C@@H]1/C=C\C=C\[C@@H](OC(=O)[C@H](C(=O)C(C(=O)[C@@H]2[C@H]1C=C[C@H]3[C@H]2[C@@H](C=C(C3)C)C)(Cl)Cl)C)C;
Properties
Chemical formula	C26H32Cl2O4
Molar mass	479.436 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chlorotonil A is a polyketide natural product produced by the myxobacterium Sorangium cellulosum So ce1525.^[2] It displays antimalarial activity in an animal model,^[3] and has in vitro antibacterial and antifungal activity.^{[citation needed]} The activity of chlorotonil A has been attributed to the gem-dichloro-1,3-dione moiety, which is a unique functionality in polyketides. In addition to its unique halogenation, the structure of chlorotonil A has also garnered interest due to its similarity to anthracimycin, a polyketide natural product with antibiotic activity against Gram-positive bacteria. Recently, structure-optimization resulted in semi-synthetic derivatives ChB1-Epo2 and Dehalogenil, molecules with significantly improved physicochemical properties.^[4]^[5]

^ "Chlorotonil A | Chemical Substance Information | J-GLOBAL". jglobal.jst.go.jp.
^ Gerth, Klaus; Steinmetz, Heinrich; Höfle, Gerhard; Jansen, Rolf (2008). "Chlorotonil A, a Macrolide with a Unique gem-Dichloro-1,3-dione Functionality from Sorangium cellulosum, So ce1525". Angewandte Chemie International Edition. 47 (3): 600–602. doi:10.1002/anie.200703993. hdl:10033/23152. PMID 18058875.
^ Held, Jana; Gebru, Tamirat; Kalesse, Markus; Jansen, Rolf; Gerth, Klaus; Müller, Rolf; Mordmüller, Benjamin (2014). "Antimalarial Activity of the Myxobacterial Macrolide Chlorotonil A". Antimicrobial Agents and Chemotherapy. 58 (11): 6378–6384. doi:10.1128/AAC.03326-14. PMC 4249382. PMID 25114138.
^ Hofer, Walter; Oueis, Emilia; Fayad, Antoine Abou; Deschner, Felix; Andreas, Anastasia; de Carvalho, Laìs Pessanha; Hüttel, Stephan; Bernecker, Steffen; Pätzold, Linda; Morgenstern, Bernd; Zaburannyi, Nestor; Bischoff, Markus; Stadler, Marc; Held, Jana; Herrmann, Jennifer; Müller, Rolf (25 July 2022). "Regio‐ and Stereoselective Epoxidation and Acidic Epoxide Opening of Antibacterial and Antiplasmodial Chlorotonils Yield Highly Potent Derivatives". Angewandte Chemie International Edition. 61 (30). doi:10.1002/ANIE.202202816. PMC 9400904.
^ Hofer, Walter; Deschner, Felix; Jézéquel, Gwenaëlle; Pessanha de Carvalho, Laìs; Abdel‐Wadood, Noran; Pätzold, Linda; Bernecker, Steffen; Morgenstern, Bernd; Kany, Andreas M.; Große, Miriam; Stadler, Marc; Bischoff, Markus; Hirsch, Anna K. H.; Held, Jana; Herrmann, Jennifer; Müller, Rolf (6 May 2024). "Functionalization of Chlorotonils: Dehalogenil as Promising Lead Compound for In Vivo Application". Angewandte Chemie International Edition. 63 (19). doi:10.1002/ANIE.202319765.

[1] "Chlorotonil A | Chemical Substance Information | J-GLOBAL". jglobal.jst.go.jp.

[2] Gerth, Klaus; Steinmetz, Heinrich; Höfle, Gerhard; Jansen, Rolf (2008). "Chlorotonil A, a Macrolide with a Unique gem-Dichloro-1,3-dione Functionality from Sorangium cellulosum, So ce1525". Angewandte Chemie International Edition. 47 (3): 600–602. doi:10.1002/anie.200703993. hdl:10033/23152. PMID 18058875.

[3] Held, Jana; Gebru, Tamirat; Kalesse, Markus; Jansen, Rolf; Gerth, Klaus; Müller, Rolf; Mordmüller, Benjamin (2014). "Antimalarial Activity of the Myxobacterial Macrolide Chlorotonil A". Antimicrobial Agents and Chemotherapy. 58 (11): 6378–6384. doi:10.1128/AAC.03326-14. PMC 4249382. PMID 25114138.

[4] Hofer, Walter; Oueis, Emilia; Fayad, Antoine Abou; Deschner, Felix; Andreas, Anastasia; de Carvalho, Laìs Pessanha; Hüttel, Stephan; Bernecker, Steffen; Pätzold, Linda; Morgenstern, Bernd; Zaburannyi, Nestor; Bischoff, Markus; Stadler, Marc; Held, Jana; Herrmann, Jennifer; Müller, Rolf (25 July 2022). "Regio‐ and Stereoselective Epoxidation and Acidic Epoxide Opening of Antibacterial and Antiplasmodial Chlorotonils Yield Highly Potent Derivatives". Angewandte Chemie International Edition. 61 (30). doi:10.1002/ANIE.202202816. PMC 9400904.

[5] Hofer, Walter; Deschner, Felix; Jézéquel, Gwenaëlle; Pessanha de Carvalho, Laìs; Abdel‐Wadood, Noran; Pätzold, Linda; Bernecker, Steffen; Morgenstern, Bernd; Kany, Andreas M.; Große, Miriam; Stadler, Marc; Bischoff, Markus; Hirsch, Anna K. H.; Held, Jana; Herrmann, Jennifer; Müller, Rolf (6 May 2024). "Functionalization of Chlorotonils: Dehalogenil as Promising Lead Compound for In Vivo Application". Angewandte Chemie International Edition. 63 (19). doi:10.1002/ANIE.202319765.