prop-2-enyl 2-(methylamino)benzoate | 1313594-88-5

• 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: prop-2-enyl 2-(methylamino)benzoate
• CAS: 1313594-88-5
• 化学式: C₁₁H₁₃NO₂
• mdl: MFCD24388378
• 分子量: 191.23
• InChiKey: PTZXYEFKLBHMHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-甲基苯唑 、 烯丙醇 在 sodium hydroxide 作用下， 以64%的产率得到prop-2-enyl 2-(methylamino)benzoate
  参考文献：
  名称：

  Antiandrogenic activity of anthranilic acid ester derivatives as novel lead structures to inhibit prostate cancer cell proliferation

  摘要：

  A plant extract from the fruits of saw palmetto, which is currently used to treat the androgen‐dependent benign prostatic hyperplasia and PCa, served as source for new structure variants. We investigated the antiandrogenic potential of an ethanolic total extract and one of its main aromatic components anthranilic acid. An androgen receptor‐antagonistic (antiandrogenic) effect of the extract was evident, and although anthranilic acid itself revealed no remarkable effect, its methyl ester, methyl anthranilate, exhibited antiandrogenic potential. Based on this chemical structure, we synthesized and investigated the antiandrogenic activity of four AnA ester derivatives, which were either novel or only little described in literature. These AnA esters inhibit the androgen‐dependent transactivation of both the wild‐type (wt) androgen receptor and the androgen receptor point mutant T877A, which often occurs in refractory PCa. Moreover, they inhibit the androgen receptor‐induced expression of the endogenous prostate‐specific antigen. Importantly, AnA esters repress the growth of human PCa cells. Deletion analyses of androgen receptor propose that the antiandrogenic effect of anthranilic acid esters is mediated by the ligand‐binding domain, most likely through direct binding, without affecting androgen receptor protein levels. Taken together, the data suggest antiandrogenic potential of anthranilic acid ester derivatives, which can serve as lead structures for novel antiandrogens.

  DOI：

  10.1111/j.1747-0285.2011.01116.x

文献信息

• SYNERGISTS
  申请人：Davidson Robert Stephen

  公开号：US20130012611A1

  公开（公告）日：2013-01-10

  Compounds of formula (I): wherein Ar represents an, optionally substituted, aryl or heteroaryl group, R represents an, optionally substituted, aryl or heteroaryl group, an optionally substituted straight or branched chain C 1.10 -alkyl, R 1 is H or methyl, X is an extender group, n is 0 or an integer between 1 and 12 inclusive, A is a polyol residue wherein the unsubstituted polyol from which the residue is derived has at least y OH groups, and y is an integer>1, can easily be prepared, and are useful as synergists in radiation curing.

  式(I)的化合物：其中Ar代表一个可选择取代的芳基或杂芳基基团，R代表一个可选择取代的芳基或杂芳基基团，一个可选择取代的直链或支链C1-10烷基，R1为H或甲基，X为延伸基团，n为0或介于1至12之间的整数，A为多元醇残基，其中未取代的多元醇至少具有y个OH基团，y为大于1的整数。这些化合物可以轻松制备，并且在辐射固化中作为协同剂非常有用。
• AMINE SYNERGISTS AND THEIR USE IN RADIATION CURING
  申请人：Sun Chemical B.V.

  公开号：EP2550250B1

  公开（公告）日：2020-06-24
• US8952190B2
  申请人：——

  公开号：US8952190B2

  公开（公告）日：2015-02-10
• [EN] SYNERGISTS<br/>[FR] AGENTS SYNERGISTES
  申请人：SUN CHEMICAL BV

  公开号：WO2011117591A2

  公开（公告）日：2011-09-29

  Compounds of formula (I): wherein Ar represents an, optionally substituted, aryl or heteroaryl group, R represents an, optionally substituted, aryl or heteroaryl group, an optionally substituted straight or branched chain C1.10-alkyl, R1 is H or methyl, X is an extender group, n is 0 or an integer between 1 and 12 inclusive, A is a polyol residue wherein the unsubstituted polyol from which the residue is derived has at least y OH groups, and y is an integer>1, can easily be prepared, and are useful as synergists in radiation curing.
• Antiandrogenic activity of anthranilic acid ester derivatives as novel lead structures to inhibit prostate cancer cell proliferation
  作者：Daniela Roell、Thomas W. Rösler、Stephanie Degen、Rudolf Matusch、Aria Baniahmad

  DOI：10.1111/j.1747-0285.2011.01116.x

  日期：2011.6

  A plant extract from the fruits of saw palmetto, which is currently used to treat the androgen‐dependent benign prostatic hyperplasia and PCa, served as source for new structure variants. We investigated the antiandrogenic potential of an ethanolic total extract and one of its main aromatic components anthranilic acid. An androgen receptor‐antagonistic (antiandrogenic) effect of the extract was evident, and although anthranilic acid itself revealed no remarkable effect, its methyl ester, methyl anthranilate, exhibited antiandrogenic potential. Based on this chemical structure, we synthesized and investigated the antiandrogenic activity of four AnA ester derivatives, which were either novel or only little described in literature. These AnA esters inhibit the androgen‐dependent transactivation of both the wild‐type (wt) androgen receptor and the androgen receptor point mutant T877A, which often occurs in refractory PCa. Moreover, they inhibit the androgen receptor‐induced expression of the endogenous prostate‐specific antigen. Importantly, AnA esters repress the growth of human PCa cells. Deletion analyses of androgen receptor propose that the antiandrogenic effect of anthranilic acid esters is mediated by the ligand‐binding domain, most likely through direct binding, without affecting androgen receptor protein levels. Taken together, the data suggest antiandrogenic potential of anthranilic acid ester derivatives, which can serve as lead structures for novel antiandrogens.