135:
20:
147:
The C(R)(N)(S) core of thioamides is planar. Using thioacetamide as representative: the C-S, C-N, and C-C distances are 1.68, 1.31, and 1.50 Å, respectively. The short C-S and C-N distances indicate multiple bonding.
390:
Trevor W. Hambley; David E. Hibbs; Peter Turner; Siân. T. Howard; Michael B. Hursthouse (2002). "Insights into
Bonding and Hydrogen Bond Directionality in Thioacetamide from the Experimental Charge Distribution".
207:. They also block iodine release from peripheral hormone. Maximum effects occur only after a month, since hormone depletion is caused by reduced synthesis, which is a slow process.
743:
941:
343:
Shabana, R.; Scheibye, S.; Clausen, K.; Olesen, S.O.; Lawesson, S.-O. (1980). "Studies on organophosphorus compounds XXXI. Synthesis of thiolactams and thioimides".
936:
736:
729:
880:
890:
885:
905:
875:
458:
171:
for the amide bond. Peptide modifications are analogues of the native peptide, which can reveal the structure-activity relationship (
870:
931:
810:
805:
915:
687:
223:
Wiberg, Kenneth B.; Rablen, Paul R. (1995). "Why Does
Thioformamide Have a Larger Rotational Barrier Than Formamide?".
63:, thioamides exhibit greater multiple bond character along the C-N bond, resulting in a larger rotational barrier.
704:
414:
Artis, Dean R.; Lipton, Mark A. (1998). "Conformations of
Thioamide-Containing Dipeptides: A Computational Study".
172:
451:
1205:
364:"3-Morpholino-2-Phenylthioacrylic Acid Morpholide and 5-(4-Bromobenzoyl-2-(4-Morpholino)-3-Phenylthiophene"
141:
1232:
959:
845:
508:
134:
1112:
780:
752:
444:
976:
763:
692:
623:
115:
80:
1003:
769:
637:
119:
591:
1013:
994:
647:
389:
8:
1227:
965:
1051:
755:
527:
180:
721:
518:
368:
321:
293:
225:
84:
1148:
1092:
1087:
1067:
1040:
840:
608:
600:
554:
549:
544:
423:
396:
263:
233:
188:
127:
40:
800:
669:
480:
176:
118:, a reaction first described in the 1870s. Alternative routes include the use of
363:
316:
284:
1138:
1128:
698:
664:
613:
161:
99:
1221:
1183:
1133:
1009:
815:
643:
488:
72:
1097:
855:
820:
493:
471:
1143:
1082:
1072:
1019:
999:
633:
578:
573:
268:
251:
175:). Analogues of peptides can also be used as drugs with an improved oral
436:
237:
1173:
900:
895:
865:
835:
503:
157:
95:
427:
1077:
830:
596:
567:
400:
196:
1188:
1178:
1102:
168:
56:
779:
975:
910:
825:
498:
467:
204:
184:
123:
76:
52:
1168:
1034:
563:
111:
60:
342:
19:
151:
751:
203:), thereby blocking uptake of iodotyrosines from the
167:Thioamides have been incorporated into peptides as
1219:
1113:
781:
977:
361:
110:Thioamides are typically prepared by treating
737:
452:
282:
222:
105:
413:
1052:
744:
730:
459:
445:
362:Rolfs, Andreas; Liebscher, Jürgen (1998).
256:Journal of the Chemical Society, Abstracts
466:
267:
18:
793:
314:
152:Thioamides in biochemistry and medicine
1220:
725:
440:
75:, which is used as a source of the
13:
942:Tetraiodothyroacetic acid (Tetrac)
14:
1244:
179:. Thioamides inhibit the enzyme
114:with phosphorus sulfides such as
1139:Ipodate sodium (sodium iopodate)
1118:Tooltip Iodothyronine deiodinase
786:Tooltip Thyroid hormone receptor
133:
23:General structure of a thioamide
982:Tooltip Sodium-iodide symporter
283:Gompper, R.; Elser, W. (1973).
156:Thioamides are also a class of
79:ion and is a building block in
407:
383:
355:
336:
308:
276:
244:
216:
1:
1206:Receptor/signaling modulators
210:
144:also gives benzylthioamides.
393:J. Chem. Soc., Perkin Trans.
187:, reducing the synthesis of
7:
142:Willgerodt-Kindler reaction
66:
43:with the general structure
10:
1249:
1057:Tooltip Thyroid peroxidase
901:Sobetirome (GC-1, GRX-431)
509:Thyroid gland preparations
331:, vol. 3, p. 332
303:, vol. 5, p. 780
252:"Preparation of thiamides"
71:A well-known thioamide is
51:are any groups (typically
16:Class of organic compounds
1197:
1161:
1111:
1050:
1033:
958:
924:
854:
762:
682:
657:
622:
589:
526:
517:
479:
378:, vol. 9, p. 99
345:Nouveau Journal de Chimie
160:that are used to control
106:Preparation and structure
98:that are used to control
753:Thyroid hormone receptor
519:Antithyroid preparations
315:Schwarz, George (1955).
624:Sodium-iodide symporter
116:phosphorus pentasulfide
317:"2,4-Dimethylthiazole"
81:heterocyclic chemistry
24:
1004:potassium perchlorate
995:Cyanogenic glycosides
638:Potassium perchlorate
22:
1014:sodium pertechnetate
866:Eprotirome (KB-2115)
859:(selective agonists)
648:Sodium pertechnetate
289:-Methyl-Δ-Pyrroline"
269:10.1039/CA8783400392
94:are also a class of
87:is a tristhioamide.
35:, but also known as
422:(47): 12200–12206.
238:10.1021/ja00113a009
122:or the reaction of
836:Tiratricol (TRIAC)
709:Never to phase III
528:Thyroid peroxidase
285:"2-Methylmercapto-
181:thyroid peroxidase
120:Lawesson's reagent
92:anti-thyroid drugs
25:
1233:Functional groups
1215:
1214:
1157:
1156:
1044:
1029:
1028:
969:
954:
953:
950:
949:
773:
719:
718:
678:
677:
428:10.1021/ja982398t
376:Collected Volumes
369:Organic Syntheses
329:Collected Volumes
322:Organic Syntheses
301:Collected Volumes
294:Organic Syntheses
226:J. Am. Chem. Soc.
85:Thiocyanuric acid
1240:
1149:Propylthiouracil
1119:
1115:
1093:Propylthiouracil
1088:Methylthiouracil
1068:Benzylthiouracil
1058:
1054:
1048:
1047:
1038:
983:
979:
973:
972:
963:
841:Triiodothyronine
791:
790:
787:
783:
777:
776:
767:
746:
739:
732:
723:
722:
609:Propylthiouracil
555:Benzylthiouracil
550:Methylthiouracil
545:Propylthiouracil
524:
523:
481:Thyroid hormones
461:
454:
447:
438:
437:
432:
431:
416:J. Am. Chem. Soc
411:
405:
404:
401:10.1039/B109353C
387:
381:
379:
372:
359:
353:
352:
340:
334:
332:
325:
312:
306:
304:
297:
280:
274:
273:
271:
248:
242:
241:
232:(8): 2201–2209.
220:
189:triiodothyronine
137:
128:hydrogen sulfide
59:). Analogous to
50:
46:
41:functional group
1248:
1247:
1243:
1242:
1241:
1239:
1238:
1237:
1218:
1217:
1216:
1211:
1193:
1153:
1117:
1107:
1056:
1037:
1025:
1022:
984:
981:
962:
946:
920:
858:
850:
846:Thyroid extract
801:Dextrothyroxine
785:
766:
758:
750:
720:
715:
714:
699:Clinical trials
674:
670:Dibromotyrosine
653:
626:
618:
595:
585:
530:
513:
475:
465:
435:
412:
408:
388:
384:
374:
360:
356:
341:
337:
327:
313:
309:
299:
281:
277:
250:
249:
245:
221:
217:
213:
202:
194:
177:bioavailability
154:
108:
69:
48:
44:
17:
12:
11:
5:
1246:
1236:
1235:
1230:
1213:
1212:
1210:
1209:
1198:
1195:
1194:
1192:
1191:
1186:
1181:
1176:
1171:
1165:
1163:
1159:
1158:
1155:
1154:
1152:
1151:
1146:
1141:
1136:
1131:
1129:Dexpropranolol
1122:
1120:
1109:
1108:
1106:
1105:
1100:
1095:
1090:
1085:
1080:
1075:
1070:
1061:
1059:
1045:
1031:
1030:
1027:
1026:
1024:
1023:
1017:
1010:Pertechnetates
1007:
997:
988:
986:
970:
956:
955:
952:
951:
948:
947:
945:
944:
939:
934:
928:
926:
922:
921:
919:
918:
913:
908:
903:
898:
893:
888:
883:
878:
873:
868:
862:
860:
852:
851:
849:
848:
843:
838:
833:
828:
823:
818:
813:
808:
803:
797:
795:
788:
774:
760:
759:
749:
748:
741:
734:
726:
717:
716:
713:
712:
711:
710:
707:
696:
690:
684:
683:
680:
679:
676:
675:
673:
672:
667:
665:Diiodotyrosine
661:
659:
655:
654:
652:
651:
641:
630:
628:
620:
619:
617:
616:
611:
605:
603:
587:
586:
584:
583:
582:
581:
576:
560:
559:
558:
557:
552:
547:
538:
536:
521:
515:
514:
512:
511:
506:
501:
496:
491:
485:
483:
477:
476:
464:
463:
456:
449:
441:
434:
433:
406:
395:(2): 235–239.
382:
354:
335:
307:
275:
243:
214:
212:
209:
200:
192:
162:thyrotoxicosis
153:
150:
107:
104:
100:thyrotoxicosis
90:Thioamides or
68:
65:
15:
9:
6:
4:
3:
2:
1245:
1234:
1231:
1229:
1226:
1225:
1223:
1208:
1207:
1204:
1200:
1199:
1196:
1190:
1187:
1185:
1184:Thyroglobulin
1182:
1180:
1177:
1175:
1172:
1170:
1167:
1166:
1164:
1160:
1150:
1147:
1145:
1142:
1140:
1137:
1135:
1134:Iopanoic acid
1132:
1130:
1127:
1124:
1123:
1121:
1116:
1110:
1104:
1101:
1099:
1096:
1094:
1091:
1089:
1086:
1084:
1081:
1079:
1076:
1074:
1071:
1069:
1066:
1063:
1062:
1060:
1055:
1049:
1046:
1042:
1036:
1032:
1021:
1018:
1015:
1011:
1008:
1005:
1001:
998:
996:
993:
990:
989:
987:
980:
974:
971:
967:
961:
957:
943:
940:
938:
935:
933:
930:
929:
927:
923:
917:
914:
912:
909:
907:
904:
902:
899:
897:
894:
892:
889:
887:
884:
882:
879:
877:
874:
872:
869:
867:
864:
863:
861:
857:
856:Thyromimetics
853:
847:
844:
842:
839:
837:
834:
832:
829:
827:
824:
822:
819:
817:
816:Levothyroxine
814:
812:
809:
807:
804:
802:
799:
798:
796:
792:
789:
784:
778:
775:
771:
765:
761:
757:
754:
747:
742:
740:
735:
733:
728:
727:
724:
708:
706:
703:
702:
700:
697:
694:
691:
689:
686:
685:
681:
671:
668:
666:
663:
662:
660:
656:
649:
645:
644:Pertechnetate
642:
639:
635:
632:
631:
629:
625:
621:
615:
612:
610:
607:
606:
604:
602:
598:
593:
588:
580:
577:
575:
572:
571:
570:derivatives:
569:
565:
562:
561:
556:
553:
551:
548:
546:
543:
542:
540:
539:
537:
534:
529:
525:
522:
520:
516:
510:
507:
505:
502:
500:
497:
495:
492:
490:
489:Levothyroxine
487:
486:
484:
482:
478:
473:
469:
462:
457:
455:
450:
448:
443:
442:
439:
429:
425:
421:
417:
410:
402:
398:
394:
386:
377:
371:
370:
365:
358:
350:
346:
339:
330:
324:
323:
318:
311:
302:
296:
295:
290:
288:
279:
270:
265:
262:: 396. 1878.
261:
257:
253:
247:
239:
235:
231:
228:
227:
219:
215:
208:
206:
198:
190:
186:
182:
178:
174:
170:
165:
163:
159:
149:
145:
143:
138:
136:
131:
129:
125:
121:
117:
113:
103:
101:
97:
93:
88:
86:
82:
78:
74:
73:thioacetamide
64:
62:
58:
54:
42:
38:
34:
30:
21:
1202:
1201:
1125:
1098:2-Thiouracil
1064:
1020:Thiocyanates
1000:Perchlorates
991:
821:Liothyronine
566:-containing
541:Thiouracils
532:
531:inhibitors (
494:Liothyronine
419:
415:
409:
392:
385:
375:
367:
357:
348:
344:
338:
328:
320:
310:
300:
292:
286:
278:
259:
255:
246:
229:
224:
218:
166:
155:
146:
139:
132:
109:
91:
89:
70:
37:thiourylenes
36:
32:
28:
26:
1144:Propranolol
1126:Inhibitors:
1083:Methimazole
1073:Carbimazole
1065:Inhibitors:
992:Inhibitors:
960:Transporter
925:Antagonists
695:from market
634:Perchlorate
579:Methimazole
574:Carbimazole
45:R−C(=S)−NRR
1228:Thioamides
1222:Categories
1174:Iodine-131
1041:inhibitors
896:Resmetirom
756:modulators
592:conversion
504:Tiratricol
211:References
55:groups or
49:R, R and R
33:thionamide
1203:See also:
1078:Genistein
881:KB-130015
831:Thyroxine
705:Phase III
693:Withdrawn
627:inhibitor
568:imidazole
533:thioamide
470:therapy (
197:thyroxine
169:isosteres
31:(rarely,
29:thioamide
1189:Tyrosine
1179:Selenium
1103:Thiourea
966:blockers
891:MB-07811
886:MB-07344
794:Agonists
764:Receptor
351:(4): 47.
124:nitriles
67:Examples
57:hydrogen
47:, where
1012:(e.g.,
1002:(e.g.,
911:VK-2809
906:VK-0214
876:KB-2611
826:Liotrix
770:ligands
614:Ipodate
499:Liotrix
468:Thyroid
205:colloid
185:thyroid
183:in the
77:sulfide
53:organyl
39:) is a
1169:Iodine
1162:Others
1035:Enzyme
985:
871:KB-141
688:WHO-EM
590:Block
564:Sulfur
195:) and
112:amides
61:amides
932:1-850
811:DITPA
806:DIMIT
658:Other
158:drugs
126:with
96:drugs
916:ZYT1
349:1980
140:The
1114:DIO
1053:TPO
978:NIS
937:NH3
782:THR
599:to
472:H03
424:doi
420:120
397:doi
264:doi
234:doi
230:117
173:SAR
164:.
1224::
701::
601:T3
597:T4
594:of
418:.
373:;
366:.
347:.
326:;
319:.
298:;
291:.
260:34
258:.
254:.
199:(T
191:(T
130::
102:.
83:.
27:A
1043:)
1039:(
1016:)
1006:)
968:)
964:(
772:)
768:(
745:e
738:t
731:v
650:)
646:(
640:)
636:(
535:)
474:)
460:e
453:t
446:v
430:.
426::
403:.
399::
380:.
333:.
305:.
287:N
272:.
266::
240:.
236::
201:4
193:3
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
