N-methyl-4-(3-aminophenyl)thiazol-2-amine | 89250-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-methyl-4-(3-aminophenyl)thiazol-2-amine
• 英文别名: 2-Thiazolamine, 4-(3-aminophenyl)-N-methyl-；4-(3-aminophenyl)-N-methyl-1,3-thiazol-2-amine
• CAS: 89250-32-8
• 化学式: C₁₀H₁₁N₃S
• 分子量: 205.283
• InChiKey: LRKWHBKBCOTUJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-4-(3-aminophenyl)thiazol-2-amine 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-(3-(2-(methylamino)thiazol-4-yl)phenyl)-4-(oct-1-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Structure activity relationship and optimization of N -(3-(2-aminothiazol-4-yl)aryl)benzenesulfonamides as anti-cancer compounds against sensitive and resistant cells

  摘要：

  We recently described a new family of bioactive molecules with interesting anti-cancer activities: the N(4-(3-aminophenyl)thiazol-2-yl)acetamides. The lead compound of the series (1) displays significant anti-proliferative and cytotoxic activities against a panel of cancer cell lines, either sensitive or resistant to standard treatments. This molecule also shows a good pharmacological profile and high in vivo potency towards mice xenografts, without signs of toxicity on the animals. In the present article, we disclose the structure-activity relationships of this lead compound, which have provided clear information about the replacement of the acetamide function and the substitution pattern of the benzenesulfonamide ring. An improved high-yielding synthetic procedure towards these compounds has also been developed. Our drug design resulted in potency enhancement of 1, our new optimized lead compound being 19. These findings are of great interest to further improve this scaffold for the development of future clinical candidates. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.03.054
• 作为产物：
  描述：

  2-溴-3'-硝基苯乙酮 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 N-methyl-4-(3-aminophenyl)thiazol-2-amine
  参考文献：
  名称：

  [EN] NEW BENZENE SULFONAMIDE THIAZOLE COMPOUNDS
  [FR] NOUVEAUX COMPOSÉS DE BENZÈNESULFONAMIDE-THIAZOLE

  摘要：

  本发明涉及一般式（1）的化合物，其中R1代表含有一个或两个融合环的C6-C10芳基，其中2至5个碳原子可以被从O、S和NR6中选择的杂原子取代，最终可以被从R6、卤素、CN、NO2、CF3、OCF3、COOR6、OCOR6、SO2NR6R7、CONR6R7、NR6R7、NR6COR7、（CH2）P-NR6R7、（CH2）P-OR6和（CH2）PSR6中选择的5至11个取代基取代，以及在适当情况下，它们的药学上可接受的盐和/或异构体、互变异构体、溶剂合物或同位素变体。这些化合物对于治疗癌症很有用。

  公开号：

  WO2014072486A1

文献信息

• [EN] 1, 3, 4-BENZOTRIAZEPIN-2-ONE SALTS AND THEIR USE AS CCK RECEPTOR LIGANDS<br/>[FR] SELS DE 1,3,4-BENZOTRIAZEPINE ET LEUR UTILISATION COMME LIGANDS DU RECEPTEUR DE CCK
  申请人：JOHNSON & JOHNSON

  公开号：WO2004101533A1

  公开（公告）日：2004-11-25

  This invention relates to pharmaceutically acceptable salts of compounds of formula (I) wherein: W is N or N+-O-; R2 is an optionally substituted C1 to C18 hydrocarbyl group wherein up to three C atoms may optionally be replaced by N, O and/or S atoms. R3 is -(CR11R12)m-X-(CR13R14)p-R9; m is 0, 1, 2, 3 or 4; p is 0, 1 or 2; X is a bond, -CR15=CR16-, -C≡C-, C(O)NH, NHC(O), C(O)NMe, NMeC(O), C(O)O, NHC(O)NH, NHC(O)O, OC(O)NH, NH, O, CO, SO2, SO2NH, C(O)NHNH, R9 is H ; C1 to C6 alkyl ; or phenyl, naphthyl, pyridyl, benzimidazolyl, indazolyl, quinolinyl, isoquinolinyl, tetrahydroisoquinolinyl, indolinyl, isoindolinyl, indolyl, isoindolyl or 2-pyridonyl substituted with -L-Q. R4 is an optionally substituted C1 to C18 hydrocarbyl group wherein up to three C atoms may optionally be replaced by N, O and/or S atoms ; and Such salts are useful, for example, for the treatment of gastrin related disorders.

  该发明涉及公式（I）化合物的药用可接受盐，其中：W为N或N+-O-；R2为可选择取代的C1至C18烃基团，其中最多三个C原子可选择地被N、O和/或S原子取代。R3为-(CR11R12)m-X-(CR13R14)p-R9；m为0、1、2、3或4；p为0、1或2；X为键、-CR15=CR16-、-C≡C-、C(O)NH、NHC(O)、C(O)NMe、NMeC(O)、C(O)O、NHC(O)NH、NHC(O)O、OC(O)NH、NH、O、CO、SO2、SO2NH、C(O)NHNH；R9为H、C1至C6烷基或苯基、萘基、吡啶基、苯并咪唑基、吲哚基、喹啉基、异喹啉基、四氢异喹啉基、吲哚啉基、异吲哚啉基、吲哚基、异吲哚基或2-吡啶酰基，取代为-L-Q。R4为可选择取代的C1至C18烃基团，其中最多三个C原子可选择地被N、O和/或S原子取代；这些盐可用于治疗胃泌素相关疾病。
• [EN] SUBSTITUTED HYDROPHOBIC BENZENE SULFONAMIDE THIAZOLE COMPOUNDS FOR USE IN TREATING CANCER<br/>[FR] COMPOSÉS DE THIAZOLE SULFONAMIDE DE BENZÈNE HYDROPHOBE SUBSTITUÉ UTILISABLES DANS LE TRAITEMENT DU CANCER
  申请人：INSERM (INSTITUT NAT DE LA SANTÉ ET DE LA RECH MÉDICALE)

  公开号：WO2017017004A1

  公开（公告）日：2017-02-02

  The present invention relates to compound of general formula (I) R1 is selected from H, aryl and alkyl, R2 is selected from H, alkyl, aryl and CO-R6; R3 is selected from H, halogen, alkyl, alkenyl, alkynyl, aryl, NHR7, NR7R8, OR7 and SR7; R4 is selected from(C6-C12) alkyl, (C2-C12) alkenyl, (C2-C12) alkynyl and (C6-C10) aryl, R5 represents H, R6, aryl, OH, OR6, O-aryl, SH, SR6, S-aryl, CN, NO2, CF3, COOR6, SO2NR6R7, CONR6R7, NH2, NHR6, NH-aryl, NR6R7, NHCOR6 or aminoacyl; R6 is alkyl optionally substituted with halogen, OH, SH, NH2, O-alkyl, S-alkyl, NH- alkyl or NH-di(alkyl); R7 and R8 identical or different are H or alkyl optionally substituted with halogen, OH, SH, NH2, O-alkyl, S-alkyl, NH-alkyl or NH-di (alkyl), their pharmaceutically acceptable salts and/or isomers, tautomers, solvates or isotopic variations thereof. The compounds are useful for the treatment of cancers.

  本发明涉及通式（I）的化合物，其中R1可选自H、芳基和烷基，R2可选自H、烷基、芳基和CO-R6；R3可选自H、卤素、烷基、烯基、炔基、芳基、NHR7、NR7R8、OR7和SR7；R4可选自（C6-C12）烷基、（C2-C12）烯基、（C2-C12）炔基和（C6-C10）芳基，R5代表H、R6、芳基、OH、OR6、O-芳基、SH、SR6、S-芳基、CN、NO2、CF3、COOR6、SO2NR6R7、CONR6R7、NH2、NHR6、NH-芳基、NR6R7、NHCOR6或氨基酰基；R6是烷基，可选地取代卤素、OH、SH、NH2、O-烷基、S-烷基、NH-烷基或NH-二（烷基）；R7和R8相同或不同，是H或可选地取代卤素、OH、SH、NH2、O-烷基、S-烷基、NH-烷基或NH-二（烷基）的烷基，其药用可接受的盐和/或同分异构体、互变异构体、溶剂合物或同位素变体。这些化合物对治疗癌症有用。
• [EN] BENZOTRIAZEPINES AS GASTRIN AND CHOLECYSTOKININ RECEPTOR LIGANDS<br/>[FR] BENZOTRIAZEPINES UTILISEES COMME LIGANDS DE RECEPTEURS DE CHOLECYSTOQUININE ET DE GASTRINE
  申请人：BLACK JAMES FOUNDATION

  公开号：WO2003041714A1

  公开（公告）日：2003-05-22

  This invention relates to a compound of formula (I) wherein: W is N or N+-O-; and R1 to R5 are as defined in the description, for use for the treatment of gastrin related disorders.

  本发明涉及式(I)的化合物，其中：W为N或N+-O-; R1至R5如描述中所定义，用于治疗胃泌素相关疾病。
• Substituted heterocyclyl-phenylformamidines and salts thereof
  申请人：Istituto de Angeli S.p.A.

  公开号：US04699915A1

  公开（公告）日：1987-10-13

  Compounds of the formula ##STR1## wherein R is hydrogen or methyl; R.sub.1 is straight or branched alkyl of 1 to 6 carbon atoms, hydroxy(alkyl of 1 to 6 carbon atoms), mono- or di-(alkoxy of 1 to 6 carbon atoms)(alkyl of 1 to 6 carbon atoms), (alkyl of 1 to 6 cabon atoms)thio(alkyl of 1 to 6 carbon atoms), cyano(alkyl of 1 to 6 carbon atoms), alkenyl, alkynyl, or cycloalkyl; R.sub.2 is hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or halogen; and X is pyrazol-3-yl, 1,2,4-triazol-3-yl, pyridin-2-yl, pyridin-3-yl, thiazol-4-yl, 2-methyl-thiazol-4-yl or 2-methylamino-thiazol-4-yl; tautomers thereof, and non-toxic, pharmacologiically acceptable acid addition salts thereof. The compounds as well as their salts are useful as antiulcerogenics and gastric acid secretion inhibitors.

  化合物的公式为##STR1## 其中R为氢或甲基；R.sub.1为1至6个碳原子的直链或支链烷基，羟基（1至6个碳原子的烷基），单或双（1至6个碳原子的烷氧基）（1至6个碳原子的烷基），（1至6个碳原子的烷基）硫（1至6个碳原子的烷基），氰基（1至6个碳原子的烷基），烯基，炔基或环烷基；R.sub.2为氢，1至3个碳原子的烷基，1至3个碳原子的烷氧基或卤素；X为吡唑-3-基，1,2,4-三唑-3-基，吡啶-2-基，吡啶-3-基，噻唑-4-基，2-甲基噻唑-4-基或2-甲氨基噻唑-4-基；其互变异构体以及其非毒性、药理学上可接受的酸盐。该化合物及其盐可用作抗溃疡剂和胃酸分泌抑制剂。
• Benzotriazepnes as gastrin and cholecystokinin receptor ligands
  申请人：McDonald Mair Iain

  公开号：US20060003993A1

  公开（公告）日：2006-01-05

  This invention relates to a compound of formula (I) wherein: W is N or N + —O − ; and R 1 to R 5 are as defined in the description, for use for the treatment of gastrin related disorders.

  本发明涉及一种化合物，其化学式为(I)，其中：W为N或N+—O−；R1至R5如描述中定义的那样，用于治疗胃泌素相关疾病。