α-methyl-N-<(phenylmethoxy)carbonyl>-D-tryptophan | 146953-09-5

• 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: α-methyl-N-<(phenylmethoxy)carbonyl>-D-tryptophan
• 英文别名: (2R)-3-(1H-indol-3-yl)-2-methyl-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 146953-09-5
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: ALMLDSRUSHJWFO-HXUWFJFHSA-N

物化性质

• 沸点：
  616.7±55.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-methyl-N-<(phenylmethoxy)carbonyl>-D-tryptophan 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 ethyl -4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoate
  参考文献：
  名称：

  Synthesis of conformationally constrained macrocyclic analogs of the potent and selective CCK-B antagonist CI-988.

  摘要：

  A series of conformationally constrained analogs of the potent CCK-B antagonist CI-988 were prepared and evaluated for their CCK-B binding affinity. A macrolactamization reaction leading to the formation of 11 to 14-membered rings was also investigated.

  DOI：

  10.1016/s0040-4020(01)86257-8
• 作为产物：
  描述：

  α-methyl-(R)-tryptophan methyl ester 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 25.0h， 生成 α-methyl-N-<(phenylmethoxy)carbonyl>-D-tryptophan
  参考文献：
  名称：

  Synthesis of conformationally constrained macrocyclic analogs of the potent and selective CCK-B antagonist CI-988.

  摘要：

  A series of conformationally constrained analogs of the potent CCK-B antagonist CI-988 were prepared and evaluated for their CCK-B binding affinity. A macrolactamization reaction leading to the formation of 11 to 14-membered rings was also investigated.

  DOI：

  10.1016/s0040-4020(01)86257-8

文献信息

• [EN] TACHYKININ ANTAGONISTS<br/>[FR] ANTAGONISTES DE TACHYKININE
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1994004494A1

  公开（公告）日：1994-03-03

  (EN) Compounds of formula (I) wherein R, R8 and R6 are possibly substituted phenyl, pyridine, thiophene, furan, naphthalene, etc.; R1 and R2 are each independently hydrogen or alkyl of from 1 to 4 atoms; R and R2, when joined by a bond, can form a ring; X is $g(a) wherein R11 is hydrogen or alkyl of from 1 to 3 carbon atoms; R3 is hydrogen or (CH2)mR13 where m is an integer of from 1 to 6 and R13 is H, CN, NH2, N(CH3)2, or NHCOCH3; n is an integer of from 1 to 2; Y is $g(b) wherein R4 is hydrogen or alkyl of from 1 to 3 carbon atoms, -CO2-, etc.; R5 and R7 are each independently hydrogen or alkyl of from 1 to 4 carbon atoms; q is an integer of from 0 to 1. The compounds are nonpeptide tachykinin antagonists and are expected to be especially useful in asthma and rheumatoid arthritis.(FR) L'invention concerne des composés ayant la formule (I), dans laquelle R, R8 et R6 représentent phenyle substitué, pyridine, thiophène, furane, napthtalène, etc. R1 et R2 représentent indépendamment hydrogène ou alkyle ayant de 1 à 4 atomes; R et R2, lorsqu'ils sont joint par une liaison, peuvent former un cycle; X est représenté par la formule $g(a) dans laquelle R11 est hydrogène ou alkyle ayant de 1 à 3 atomes de carbone; R3 représente hydrogène ou (CH2)mR13 dans laquelle m est un nombre entier compris entre 1 et 6 et R13 représente H, CN, NH2, N(CH3)2, ou NHCOCH3; n est un nombre entier égal à 1 ou 2; Y est représenté par la formule $g(b) dans laquelle R4 est hydrogène ou alkyle ayant de 1 à 3 atomes de carbone, -CO2-, etc. R5 et R7 représentent indépendamment hydrogène ou alkyle ayant de 1 à 4 atomes de carbone; q est un nombre entier de 0 à 1; les composés sont des antagonistes de tachykinine non peptides et peuvent être particulièremet utiles pour traiter l'asthme et le rhumatisme articulaire.

  (中) 公式（I）中的化合物，其中R，R8和R6可能是取代的苯基，吡啶，噻吩，呋喃，萘等；R1和R2分别独立地为氢或1至4个原子的烷基；当R和R2通过键结合时，可以形成环；X是$ g（a），其中R11为1至3个碳原子的氢或烷基；R3为氢或（CH2）mR13，其中m为1至6的整数，R13为H，CN，NH2，N（CH3）2或NHCOCH3；n为1至2的整数；Y是$ g（b），其中R4为氢或1至3个碳原子的烷基，-CO2-等；R5和R7各自独立地为氢或1至4个碳原子的烷基；q为0至1的整数。这些化合物是非肽类缩氨酸拮抗剂，预计在哮喘和类风湿性关节炎等方面特别有用。
• New Active Series of Growth Hormone Secretagogues
  作者：Vincent Guerlavais、Damien Boeglin、Delphine Mousseaux、Catherine Oiry、Annie Heitz、Romano Deghenghi、Vittorio Locatelli、Antonio Torsello、Corrado Ghé、Filomena Catapano、Giampiero Muccioli、Jean-Claude Galleyrand、Jean-Alain Fehrentz、Jean Martinez

  DOI：10.1021/jm020985q

  日期：2003.3.1

  New growth hormone secretagogue (GHS) analogues were synthesized and evaluated for growth hormone releasing activity. This series derived from EP-51389 is based on a gem-diamino structure. Compounds that exhibited higher in vivo GH-releasing potency than hexarelin in rat (subcutaneous administration) were then tested per os in beagle dogs and for their binding affinity to human pituitary GHS receptors and to hGHS-R 1a. Compound 7 (JMV 1843, H-Aib-(D)-Trp-(D)-gTrp-formyl) showed high potency in these tests and was selected for clinical studies.(1)
• US6066633A
  申请人：——

  公开号：US6066633A

  公开（公告）日：2000-05-23
• Synthesis of conformationally constrained macrocyclic analogs of the potent and selective CCK-B antagonist CI-988.
  作者：Gary L. Bolton、Bruce D. Roth、B.K. Trivedi

  DOI：10.1016/s0040-4020(01)86257-8

  日期：1993.1

  A series of conformationally constrained analogs of the potent CCK-B antagonist CI-988 were prepared and evaluated for their CCK-B binding affinity. A macrolactamization reaction leading to the formation of 11 to 14-membered rings was also investigated.