N-[2-(1-acetyl-piperidin-4-ylamino)-benzyl]-N-[2-(4-chloro-phenoxy)-phenyl]-acetamide | 1158909-74-0

• 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-[2-(1-acetyl-piperidin-4-ylamino)-benzyl]-N-[2-(4-chloro-phenoxy)-phenyl]-acetamide
• 英文别名: N-[[2-[(1-acetylpiperidin-4-yl)amino]phenyl]methyl]-N-[2-(4-chlorophenoxy)phenyl]acetamide
• CAS: 1158909-74-0
• 化学式: C₂₈H₃₀ClN₃O₃
• 分子量: 492.017
• InChiKey: ZFHJZFOUUJQRNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [2-(4-chloro-phenoxy)-phenyl]-2-nitro-benzylamine 在 三乙酰氧基硼氢化钠 、 铁粉 、 氯化铵 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 20.5h， 生成 N-[2-(1-acetyl-piperidin-4-ylamino)-benzyl]-N-[2-(4-chloro-phenoxy)-phenyl]-acetamide
  参考文献：
  名称：

  取代的芳基苄胺作为 17β-羟基类固醇脱氢酶 3 型的有效和选择性抑制剂

  摘要：

  17β-羟基类固醇脱氢酶 3 型 (17β-HSD3) 在睾丸和精囊中高水平表达；它也存在于前列腺组织中，并参与性腺和非性腺睾酮的生物合成。该酶是膜结合的，还没有晶体结构。使用先前建立的同源模型和对接研究，通过基于结构的设计，设计并合成了基于选择性芳基苄胺的抑制剂作为前列腺癌治疗的潜在药物。使用N- (2-([2-(4-氯苯氧基)苯基氨基]甲基)苯基)乙酰胺 ( 1 )发现了有效的、选择性的、低纳摩尔 IC 50 17β-HSD3 抑制剂。最有效的化合物具有大约 75 nM 的 IC 50值。化合物29 , N -[2-(1-Acetylpiperidin-4-ylamino)benzyl] -N -[2-(4-chlorophenoxy)phenyl]acetamide, IC 50为 76 nM，而化合物30 , N -(2- (1-[2-(4-氯苯氧基)-苯基氨基]乙基)苯基)乙酰胺，IC

  DOI：

  10.3390/molecules26237166

文献信息

• COMPOUND CAPABLE OF INHIBITING 17-BETA HYDROXYSTERIOD DEHYDROGENASE
  申请人：Vicker Nigel

  公开号：US20100286204A1

  公开（公告）日：2010-11-11

  There is provided a compound having Formula I wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently selected from (a) H, (b) R 13 , —OC(R 13 ) 3 , —OCH(R 13 ) 2 , —OCH 2 R 13 , C(R 13 ) 3 , —CH(R 13 ) 2 , or —CH 2 R 13 wherein R 13 is a halogen; (c) —CN; (d) optionally substituted alkyl, (e) optionally substituted heteroalkyl; (f) optionally substituted aryl; (g) optionally substituted heteroaryl; (h) optionally substituted arylalkyl; (i) optionally substituted heteroarylalkyl; (j) hydroxy; (k) alkoxy; (l) aryloxy; (m) —SO 2 -alkyl; and (n) —N(R 14 )C(O)R 15 , wherein R 14 and R 15 are independently selected from H and hydrocarbyl, wherein the optional substituents of (d) (e) (f) (h) and (i) are selected from the group consisting of: C 1-6 alkyl, halo, cyano, nitro, haloalkyl, hydroxy, C 1-6 alkoxy, carboxy, carboxyalkyl, carboxamide, mercapto, amino, alkylamino, dialkylamino, sulfonyl, sulfonamido, aryl and heteroaryl; wherein n and p are independently selected from 0 and 1; X is an optional group selected from O, S, S=0, S(═O) 2 , C═O, S(═O) 2 NR 16 , C═ONR 17 , NR 18 , in which R 16 , R 17 , and R 18 are independently selected from H and hydrocarbyl, R 10 is selected from H and hydrocarbyl, R 11 is selected from CR 19 R 20 and C═O, in which R 19 and R 20 are independently selected from H and hydrocarbyl, R 12 is selected from a substituted five or six membered carbon rings optionally containing one or more hetero atoms selected from N, S, and O and optionally having fused thereto a further ring, and wherein the one or more substituents are selected from hydrocarbyl groups.

  提供了一种化合物，其具有以下化学式I，其中R1、R2、R3、R4、R5、R6、R7、R8和R9分别独立地选择自(a) H、(b) R13、-OC(R13)3、-OCH(R13)2、-OCH2R13、C(R13)3、-CH(R13)2或-CH2R13，其中R13是卤素；(c) -CN；(d) 可选取代的烷基；(e) 可选取代的杂环烷基；(f) 可选取代的芳基；(g) 可选取代的杂芳基；(h) 可选取代的芳基烷基；(i) 可选取代的杂芳基烷基；(j) 羟基；(k) 烷氧基；(l) 芳氧基；(m) -SO2-烷基；和(n) -N(R14)C(O)R15，其中R14和R15独立地选择自H和烃基，(d)、(e)、(f)、(h)和(i)的可选取代基团选择自以下群中的一种：C1-6烷基、卤素、氰基、硝基、卤代烷基、羟基、C1-6烷氧基、羧基、羧基烷基、羧酰胺基、巯基、氨基、烷基氨基、二烷基氨基、磺酰基、磺酰胺基、芳基和杂芳基；其中n和p独立地选择自0和1；X是可选的基团，选择自O、S、S=0、S(═O)2、C═O、S(═O)2NR16、C═ONR17、NR18，其中R16、R17和R18独立地选择自H和烃基，R10选择自H和烃基，R11选择自CR19R20和C═O，其中R19和R20独立地选择自H和烃基，R12选择自可选取代的含有一个或多个杂原子(N、S和O)的取代的五元或六元碳环，且可选择进一步融合环，其中一个或多个取代基团选择自烃基团。
• US8558028B2
  申请人：——

  公开号：US8558028B2

  公开（公告）日：2013-10-15
• [EN] COMPOUND<br/>[FR] COMPOSÉ
  申请人：STERIX LTD

  公开号：WO2009066072A2

  公开（公告）日：2009-05-28

  There is provided a compound having Formula (I), wherein each of R1, R2, R3, R4, R5, R6, R7, R8 and R9 are independently selected from (a) H, (b) R13, -OC(R13)3, -OCH(R13)2, -OCH2R13, -C(R13)3, -CH(R13)2, or -CH2R13 wherein R13 is a halogen; (c) -CN; (d) optionally substituted alkyl, (e) optionally substituted heteroalkyl; (f) optionally substituted aryl; (g) optionally substituted heteroaryl; (h) optionally substituted arylalkyl; (i) optionally substituted heteroarylalkyl; (j) hydroxy; (k) alkoxy; (I) aryloxy; (m) -SO2-alkyl; and (n) -N(R14)C(O)R15, wherein R14 and R15 are independently selected from H and hydrocarbyl, wherein the optional substituents of (d) (e) (T) (h) and (i) are selected from the group consisting of: C1-6 alkyl, halo, cyano, nitro, haloalkyl, hydroxy, C1-6 alkoxy, carboxy, carboxyalkyl, carboxamide, mercapto, amino, alkylamino, dialkylamino, sulfonyl, sulfonamido, aryl and heteroaryl; wherein n and p are independently selected from 0 and 1; X is an optional group selected from O, S, S=O, S(=O)2, C=O, S(=O)2NR16, C=ONR17, NR18, in which R16, R17, and R18 are independently selected from H and hydrocarbyl, R10 is selected from H and hydrocarbyl, R11 is selected from CR19R20 and C=O, in which R19 and R20 are independently selected from H and hydrocarbyl, R12 is selected from a substituted five or six membered carbon rings optionally containing one or more hetero atoms selected from N, S, and O and optionally having fused thereto a further ring, and wherein the one or more substituents are selected from hydrocarbyl groups.
• Substituted Aryl Benzylamines as Potent and Selective Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 3
  作者：Nigel Vicker、Helen V. Bailey、Joanna M. Day、Mary F. Mahon、Andrew Smith、Helena J. Tutill、Atul Purohit、Barry V. L. Potter

  DOI：10.3390/molecules26237166

  日期：——

  low nanomolar IC50 17β-HSD3 inhibitors were discovered using N-(2-([2-(4-chlorophenoxy)phenylamino]methyl)phenyl)acetamide (1). The most potent compounds have IC50 values of approximately 75 nM. Compound 29, N-[2-(1-Acetylpiperidin-4-ylamino)benzyl]-N-[2-(4-chlorophenoxy)phenyl]acetamide, has an IC50 of 76 nM, while compound 30, N-(2-(1-[2-(4-chlorophenoxy)-phenylamino]ethyl)phenyl)acetamide, has an IC50

  17β-羟基类固醇脱氢酶 3 型 (17β-HSD3) 在睾丸和精囊中高水平表达；它也存在于前列腺组织中，并参与性腺和非性腺睾酮的生物合成。该酶是膜结合的，还没有晶体结构。使用先前建立的同源模型和对接研究，通过基于结构的设计，设计并合成了基于选择性芳基苄胺的抑制剂作为前列腺癌治疗的潜在药物。使用N- (2-([2-(4-氯苯氧基)苯基氨基]甲基)苯基)乙酰胺 ( 1 )发现了有效的、选择性的、低纳摩尔 IC 50 17β-HSD3 抑制剂。最有效的化合物具有大约 75 nM 的 IC 50值。化合物29 , N -[2-(1-Acetylpiperidin-4-ylamino)benzyl] -N -[2-(4-chlorophenoxy)phenyl]acetamide, IC 50为 76 nM，而化合物30 , N -(2- (1-[2-(4-氯苯氧基)-苯基氨基]乙基)苯基)乙酰胺，IC