N-(cyclohexylcarbonyl)-D-phenylalanine | 85856-40-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(cyclohexylcarbonyl)-D-phenylalanine
• 英文别名: (R)-2-(cyclohexanecarboxamido)-3-phenylpropanoic acid；(2R)-2-(cyclohexanecarbonylamino)-3-phenylpropanoic acid
• CAS: 85856-40-2
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: TYZXWNYMZXLYSH-CQSZACIVSA-N

物化性质

• 熔点：
  170-171 °C
• 沸点：
  517.0±39.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,E)-N-(3-(7-hydroxy-4-methyldeca-3,9-dien-1-yl)-5-methoxyphenyl)non-8-enamide 、 N-(cyclohexylcarbonyl)-D-phenylalanine 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 以38%的产率得到(4R,7E)-10-(3-methoxy-5-(non-8-enamido)phenyl)-7-methyldeca-1,7-dien-4-yl (2R)-2-(cyclohexanecarboxamido)-3-phenylpropanoate
  参考文献：
  名称：

  Monoenomycin: A Simplified Trienomycin A Analogue That Manifests Anticancer Activity

  摘要：

  Macrocydic natural products are a powerful class of leadlike chemical entities. Despite commonly violating Lipinski's "rule of 5", these compounds often demonstrate superior druglike physicochemical and pharmacokinetic attributes when compared to their acyclic counterparts. However, the elaborate structural architectures of such molecules require rigorous synthetic investigation that complicates analogue development and their application to drug discovery programs. To circumvent these limitations, a conformation-based approach using limited structure-activity relationships and molecular modeling was implemented to design simplified analogues of trienomycin A, in which the corresponding analogues could be prepared in a succinct manner to rapidly identify essential structural components necessary for biological activity. Trienomycin A is a member of the ansamycin family of natural products that possesses potent anticancer activity. These studies revealed a novel trienomycin A analogue, rnonoenomycin, which manifests potent anticancer activity.

  DOI：

  10.1021/ml200108y
• 作为产物：
  描述：

  D-苯丙氨酸甲酯 在 sodium hydroxide 、 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N-(cyclohexylcarbonyl)-D-phenylalanine
  参考文献：
  名称：

  N-（环己基羰基）-D-苯丙氨酸和相关化合物。一类新的口服降糖药。2。

  摘要：

  已经合成了一系列N-（环己基羰基）-D-苯丙氨酸的类似物（5），并评估了它们的降血糖活性。研究了酰基部分的活性与三维结构之间的关系，该关系通过高分辨率1H NMR光谱学和MNDO计算来表征。还通过比较苯丙氨酸衍生物的对映异构体，脱羧衍生物，酯和酰胺的活性，研究了苯丙氨酸部分的羧基的作用。因此，阐明了具有降血糖活性的结构要求，并获得了高活性化合物N-[（反式-4-异丙基环己基）羰基] -D-苯丙氨酸（13），其口服后血糖降低了20％。禁食正常小鼠的最大剂量为1.6 mg / kg。

  DOI：

  10.1021/jm00127a006

文献信息

• N-Acylphenylalanines and related compounds. A new class of oral hypoglycemic agents
  作者：Hisashi Shinkai、Koji Toi、Izumi Kumashiro、Yoshiko Seto、Mariko Fukuma、Katsuaki Dan、Shigeshi Toyoshima

  DOI：10.1021/jm00119a007

  日期：1988.11

  N-Benzoyl-DL-phenylalanine (1) was found to possess hypoglycemic activity. A series of the analogues of compound 1 were prepared and evaluated for their blood glucose lowering activity. Both the steric effects of the phenylalanine moiety and the effects of variations in the acyl moiety were investigated. This study elucidated some of the structure-activity relationships and led to the development of

  N-苯甲酰基-DL-苯丙氨酸（1）被发现具有降血糖活性。制备了一系列化合物1的类似物，并评估了它们的降血糖活性。研究了苯丙氨酸部分的空间影响和酰基部分变化的影响。这项研究阐明了一些构效关系，并导致了N-（4-乙基苯甲酰基）-D-苯丙氨酸（34）的开发，其效力是初始化合物1的50倍。
• [EN] NOVEL FORM OF N-(TRANS-4-ISOPROPYLCYCLOHEXYLCARBONYL)-D-PHENYLALANINE<br/>[FR] NOUVELLE FORME DE N-(TRANS-4-ISOPROPYLCYCLOHEXYLCARBONYL)-D-PHENYLALANINE
  申请人：BIOCON LTD

  公开号：WO2003093222A1

  公开（公告）日：2003-11-13

  Novel polymorph Form C of N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine is produced having different infra red spectrum and X-ray diffraction patterns from previously known forms of the compound.

  新型多晶形态C的N-(trans-4-异丙基环己基甲酰)-D-苯丙氨酸已被制备出来，其红外光谱和X射线衍射图样与先前已知的该化合物形态不同。
• Novel form of n-(trans-4-isopropylcyclohexylcarbonyl)-d-phenylalanine
  申请人：Rajamahendra Shanmughasamy

  公开号：US20050165108A1

  公开（公告）日：2005-07-28

  The present invention relates to a novel crystalline form of N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine and methods for preparing the same.

  本发明涉及一种新型晶体形式的N-(trans-4-异丙基环己基甲酰)-D-苯丙氨酸及其制备方法。
• SHINKAI, HISASHI;NISHIKAWA, MASAHIKO;SATO, YUSUKE;TOI, KOJI;KUMASHIRO, IZ+, J. MED. CHEM., 32,(1989) N, C. 1436-1441
  作者：SHINKAI, HISASHI、NISHIKAWA, MASAHIKO、SATO, YUSUKE、TOI, KOJI、KUMASHIRO, IZ+

  DOI：——

  日期：——
• NOVEL STABLE CRYSTAL FORM OF N-TRANS-4-ISOPROPYLCYCLOHEXYL CARBONYL)-D-PHENYLALANINE AND PROCESS OF PREPARATION
  申请人：Alembic Limited

  公开号：EP1435912A1

  公开（公告）日：2004-07-14