4-Phenyl-2-piperidino-thiazol | 34587-25-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-Phenyl-2-piperidino-thiazol
• 英文别名: 2-piperidino-4-phenyl-thiazole；1-(4-phenylthiazol-2-yl)piperidine；4-Phenyl-2-piperidinylthiazol；4-Phenyl-2-piperidyl-thiazol；2-Piperidino-5-phenylthiazol；1-(4-phenyl-2-thiazolyl)Piperidine；4-phenyl-2-piperidin-1-yl-1,3-thiazole
• CAS: 34587-25-2
• 化学式: C₁₄H₁₆N₂S
• mdl: MFCD01208708
• 分子量: 244.36
• InChiKey: QWDSVKYWKIRRBD-UHFFFAOYSA-N

物化性质

• 熔点：
  71.5-72.5 °C(Solv: methanol (67-56-1))
• 沸点：
  403.3±38.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Phenyl-2-piperidino-thiazol 以 四氢呋喃 为溶剂， 生成 α-Ethoxy-β-(4-phenyl-2-piperidino-thiazol-5-yl)-acrylsaeure
  参考文献：
  名称：

  Syntheses of 2-disubstituted-amino-4-arylthiazol-5-ylalkanoic acids.

  摘要：

  研究了一种合成 2-二取代-氨基-4-芳基噻唑-5-基烷酸（3）的新方法。S-(α-benzoyl-β-ethoxycarbonyl) 1-哌啶硫代碳酸乙酯（5a）在高氯酸-乙酸酐水溶液存在下脱水生成 4-乙氧羰基-甲基-5-苯基-2-哌啶基-1，3-氧硫杂环戊烷高氯酸盐（1a）。氨与 1a 发生亲核反应，得到 5-乙氧羰基甲基-4-苯基-2-哌啶噻唑（2a）。2a 在酸催化下水解，得到盐酸盐 3a。酸 (3) 也是通过经典的 Hantzsch 方法合成的。这些烷酸作为抗炎剂对角叉菜胶诱发的大鼠脓肿进行了评估。

  DOI：

  10.1248/cpb.25.2292
• 作为产物：
  描述：

  piperidine-1-carboximidothioic acid 2-oxo-2-phenyl-ethyl ester 以 乙酸乙酯 为溶剂， 生成 4-Phenyl-2-piperidino-thiazol
  参考文献：
  名称：

  Reactions of 2-dialkylamino-5-phenyl-1,3-oxathiolium cation with nucleophiles containing an amino group.

  摘要：

  2-二烷基氨基-1, 3-氧硫杂环鎓（I）与氨基亲核物的反应可以简单地获得多种杂环化合物。噻二嗪和噻唑分别很容易从与肼和氨的反应中获得。同时还分离出了易于转化为噻唑的中间产物。对 1 与芳香胺反应的研究表明，根据反应条件的不同，会生成开环酮和 2-芳基亚氨基-1，3-氧硫杂环戊烷。I 与芳香胺和脂肪胺在沸腾的冰乙酸中发生反应，生成 2-亚氨基噻唑啉衍生物。

  DOI：

  10.1248/cpb.26.3017

文献信息

• Studies of heterocyclic compounds. V. Synthesis of 5,6-dihydrothiazolo(2,3-b)thiazolium salts and their reactions with amines. A new synthesis of 2-aminothiazoles.
  作者：HIROKO OHTSUKA、HATSUNORI TOYOFUKU、TADASHI MIYASAKA、KIICHI ARAKAWA

  DOI：10.1248/cpb.23.3234

  日期：——

  5, 6-Dihydrothiazolo [2, 3-b] thiazolium salts (1a-d) were synthesized from 2-mercapto-thiazoline and α-haloketones. The reaction of 1 with a secondary amine gave 2-aminothiazole (7a-1) with the liberation of thiirane (9) via an unstable adduct, 7a-amino-2, 3, 5, 6-tetrahydrothiazolo [2, 3-b] thiazole (8a-g). The reaction of 1 with a primary amine afforded 3-(2-mercaptoethyl)-4-thiazolin-2-imine (10) and/or its disulfide (11). The reaction of 1 with an amine was concluded to be initiated by the attack of the reagent on C-7a.

  5, 6-二氢噻唑 [2, 3-b] 噻唑鎓盐（1a-d）是通过2-巯基噻唑啉和α-卤酮合成的。1与二级胺的反应生成了2-氨基噻唑（7a-1），同时通过不稳定的加合物7a-氨基-2, 3, 5, 6-四氢噻唑 [2, 3-b] 噻唑（8a-g）释放出噻烷（9）。1与一级胺的反应产生了3-(2-巯基乙基)-4-噻唑啉-2-亚胺（10）和/或其二硫化物（11）。关于1与胺的反应，结论是反应的起始是由于试剂对C-7a的攻击。
• 2-Hetaryl Derivatives of 3-Oxo-3,4-dihydro-2<i>H</i>-1,4-benzothiazine
  作者：Konstantin G. Nazarenko、Nataliya A. Shtil、Alexander N. Chernega、Miron O. Lozinskii、Andrey A. Tolmachev

  DOI：10.1055/s-2004-822375

  日期：——

  A new approach for the synthesis of 2-hetaryl derivatives of 3-oxo-3,4-dihydro-2H-1,4-benzothiazines is described. 2-Chloro derivatives of 2a,b were reacted with electron-rich heterocycles 3-14 under basic catalysis (with a slight excess of Et3N) to provide the substitution products 16-36. In the reaction of 2b with 14 and 15, an intermolecular cyclization took place between the amino and ethoxycarbonyl groups, resulting in spiro compounds 35 and 36, respectively.

  描述了一种合成3-氧-3,4-二氢-2H-1,4-苯并噻嗪的2-杂芳衍生物的新方法。2-氯衍生物2a和2b在碱性催化（略微过量的三乙胺）下与富电子的杂环化合物3-14反应，得到取代产物16-36。在2b与14和15的反应中，氨基和乙氧基羧基之间发生了分子间环化，分别生成了螺旋化合物35和36。
• N-SULFONYL THIAZOLYLPIPERAZINE DERIVATIVES AND RELATED N-SULFONYL HETEROCYCLIC DERIVATIVES FOR THE TREATMENT OF NEURO DEGENERATIVE DISEASES
  申请人：GRIFFIOEN Gerard

  公开号：US20100197703A1

  公开（公告）日：2010-08-05

  This invention provides thiazolylpiperazine derivatives, and N-sulfonyl heterocyclic derivatives including phenyl- and benzyl-thiazolylpiperidine derivatives, and pharmaceutically acceptable salts thereof, which are useful active ingredients for administration in a method for the treatment of an α-synucleopathy such as Parkinson's disease, diffuse Lewy body disease, traumatic brain injury, amyotrophic lateral sclerosis, Niemann-Pick disease, Hallervorden-Spatz syndrome, Down syndrome, neuroaxonal dystrophy, multiple system atrophy and Alzheimer's disease. This invention also provides methods for making such derivatives, and pharmaceutical compositions including such derivatives together with pharmaceutically acceptable excipients.

  该发明提供了噻唑基哌嗪衍生物，以及包括苯基和苄基噻唑基哌啶衍生物的N-磺酰杂环衍生物，以及其药学上可接受的盐，这些是用于治疗α-突触核蛋白病的有效活性成分，如帕金森病、弥漫性小体病、创伤性脑损伤、肌萎缩侧索硬化症、尼曼-匹克病、哈勒沃登-施帕茨综合征、唐氏综合征、神经轴突萎缩、多系统萎缩和阿尔茨海默病的治疗方法。该发明还提供了制备这些衍生物的方法，以及包括这些衍生物和药学上可接受的辅料的药物组合物。
• [EN] HUMAN ANDROGEN RECEPTOR DNA-BINDING DOMAIN (DBD) COMPOUNDS AS THERAPEUTICS AND METHODS FOR THEIR USE<br/>[FR] COMPOSÉS CIBLANT LE DOMAINE DE LIAISON À L'ADN (DBD) DU RÉCEPTEUR DES ANDROGÈNES HUMAIN SERVANT D'AGENTS THÉRAPEUTIQUES ET PROCÉDÉS POUR LEUR UTILISATION
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2015120543A1

  公开（公告）日：2015-08-20

  A compound having the structure of Formula I, wherein A is a substituted or unsubstituted aryl or heteroaryl group, D is a substituted or unsubstituted 5- or 6-mcmbcrcd heteroaryl or heterocyclyl group and E is a substituted or unsubstituted aryl, heteroaryl, cycloalkyl or heterocyclyl group. The compounds are used for the treatment of androgen modulated indications including cancer (prostate, breast, ovarian, endometrial or blader cancer), hair loss, acne, hirsutism, ovarian cysts, polycystic ovary disease, precocious puberty and age related macular degeneration. The use of the compounds for the manufacture of a medicament for modulating AR activity, a method of treatment using such compounds and a pharmaceutical composition and a commercial package comprising said compounds arc also described.

  一种具有公式I结构的化合物，其中A是取代或未取代的芳基或杂芳基基团，D是取代或未取代的5-或6-成员杂芳基或杂环基基团，E是取代或未取代的芳基，杂芳基，环烷基或杂环基基团。这些化合物用于治疗雄激素调节的症状，包括癌症（前列腺，乳腺，卵巢，子宫内膜或膀胱癌），脱发，痤疮，多毛症，卵巢囊肿，多囊卵巢综合症，早熟和年龄相关性黄斑变性。还描述了使用这些化合物制造调节雄激素受体活性的药物、使用这些化合物的治疗方法、以及包含这些化合物的制药组合物和商业包装。
• Human androgen receptor DNA-binding domain (DBD) compounds as therapeutics and methods for their use
  申请人：The University of British Columbia

  公开号：US10011573B2

  公开（公告）日：2018-07-03

  A compound having the structure of Formula I, wherein A is a substituted or unsubstituted aryl or heteroaryl group, D is a substituted or unsubstituted 5- or 6-membered heteroaryl or heterocyclyl group and E is a substituted or unsubstituted aryl, heteroaryl, cycloalkyl or heterocyclyl group. The compounds are used for the treatment of androgen modulated indications including cancer (prostate, breast, ovarian, endometrial or bladder cancer), hair loss, acne, hirsutism, ovarian cysts, polycystic ovary disease, precocious puberty and age related macular degeneration. The use of the compounds for the manufacture of a medicament for modulating AR activity, a method of treatment using such compounds and a pharmaceutical composition and a commercial package comprising said compounds are also described.

  具有式 I 结构的化合物，其中 A 是取代或未取代的芳基或杂芳基，D 是取代或未取代的 5 或 6 元杂芳基或杂环基，E 是取代或未取代的芳基、杂芳基、环烷基或杂环基。这些化合物可用于治疗雄激素调节适应症，包括癌症（前列腺癌、乳腺癌、卵巢癌、子宫内膜癌或膀胱癌）、脱发、痤疮、多毛症、卵巢囊肿、多囊卵巢病、性早熟和老年性黄斑变性。此外，还描述了这些化合物在制造调节 AR 活性的药物中的用途、使用这些化合物的治疗方法以及包含上述化合物的药物组合物和商业包装。