β,β-dimethyl-S-(4-methylbenzyl)-β-mercaptopropionic acid | 104532-40-3

• 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: β,β-dimethyl-S-(4-methylbenzyl)-β-mercaptopropionic acid
• 英文别名: S-(4-methylbenzyl)deaminopenicillamine；3-Methyl-3-{[(4-methylphenyl)methyl]sulfanyl}butanoic acid；3-methyl-3-[(4-methylphenyl)methylsulfanyl]butanoic acid
• CAS: 104532-40-3
• 化学式: C₁₃H₁₈O₂S
• 分子量: 238.351
• InChiKey: NUYZXOYQOUPQES-UHFFFAOYSA-N

物化性质

• 沸点：
  378.0±30.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  BOC-L-脯氨酸 、 BOC-L-天冬酰胺 、 Boc-O-甲基-L-酪氨酸 、 β,β-dimethyl-S-(4-methylbenzyl)-β-mercaptopropionic acid 、 alkaline earth salt of/the/ methylsulfuric acid 生成 cyclo-(β,β-pentamethylene-β-mercaptopropionyl)-Tyr(OMe)-Phe-Val-Asn-Cys-Pro-Lys-D-Tyr-NH2
  参考文献：
  名称：

  潜在的加压素光亲和标记的制备和生物活性。

  摘要：

  肽激素加压素（VP）的几种潜在的光亲和性类似物是通过经典的固相肽合成方法，使用两种不同的途径制备的。通过在光标记位置引入（a）Nar保护的氨基苯丙氨酸或（b）硝基苯丙氨酸来构建肽序列。裂解后和纯化前，在途径a中完成了向叠氮基肽的转化，在途径b中，由少量纯化的含硝基苯丙氨酸的前体肽完成了转化。使用从大鼠肝细胞制备的膜测量V1受体结合特性。通过将叠氮基或硝基基团引入位置3的芳族侧链，可以消除激动剂VP结构的结合潜力。制备了β-二烷基-Cys1型VP拮抗剂结构，该结构的光活化部分位于位置2，碘化残基位于位置9。一种特定的化合物[Dmpa1，Phe（N3）2，Val4，Lys8，D-Tyr9] VP（ 8），在位置1包含β，β-二甲基-β-巯基丙酸，在放射性碘化（Kd = 4.8 +/- 1.9 x 10（-10）M）和非碘化形式（Kd = 6.4）上均具有优异的结合性能+/- 0.98 x 10

  DOI：

  10.1021/jm00079a020
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 、 4-甲基苄基硫醇 以 various solvent(s) 为溶剂， 反应 13.0h， 以53%的产率得到β,β-dimethyl-S-(4-methylbenzyl)-β-mercaptopropionic acid
  参考文献：
  名称：

  Structure-activity studies of a novel bicyclic oxytocin antagonist

  摘要：

  In this report, we describe structure-activity studies of the bicyclic oxytocin antagonist [Mpa1,cyclo(Glu4,Lys8)]oxytocin. The monocylic analogue [dPen1,Glu4,Lys8)]oxytocin was a weak oxytocin antagonist with a pA2 Value of 5.8 in the uterotonic assay. Bicyclization of this analogue yielded [dPen1,cyclo(Glu4,Lys8)]oxytocin, a potent antagonist of oxytocin in the uterotonic assay (pA2 8.74) with a potency 3 times greater than that of [Mpa1,cyclo(Glu4,Lys8)]oxytocin. [dPen1,cyclo(Glu4,Lys8)]oxytocin also was a weak antagonist in the pressor assay with a pA2 of 6.3. To establish if the potent antagonistic effects of these bicyclic compounds was because of the lactam ring or merely the result of obtaining an optimal degree of lipophilicity of the side chains in positions 4 and 8, we synthesized a series of analogues containing neutral and/or charged groups on these side chains. Monocyclic derivatives of [Mpa1,Gln4,Lys(CHO)8]oxytocin were moderate to weak agonists of oxytocin all following classical structure-activity profiles of oxytocin. The monocyclic derivatives of [dPen1,Gln4,Lys(CHO)8]oxytocin were antagonists of oxytocin which was attributed to the dPen1 substitution. However, the potency of all of these latter derivatives was at least 1 order of magnitude less than [dPen1,cyclo(Glu4,Lys8)]oxytocin. These results suggest that the potent antagonistic properties of the bicyclic analogues [Mpa1,cyclo(Glu4,Lys8)]oxytocin and [dPen1,cyclo(Glu4,Lys8)]oxytocin can be attributed to the effect of the lactam bridge on the conformational flexibility and topographical properties of the analogues, rendering them more favorable for binding to the receptor in such a manner as to prevent transduction of a biological response.

  DOI：

  10.1021/jm00087a009

文献信息

• ANTI-EFNA4 ANTIBODY-DRUG CONJUGATES
  申请人：Pfizer, Inc.

  公开号：US20150125472A1

  公开（公告）日：2015-05-07

  The present invention provides for anti-EFNA4 antibody-drug conjugates and methods for preparing and using the same.
• INTERMEDIATES AND METHODS FOR SYNTHESIZING CALICHEAMICIN DERIVATIVES
  申请人：Pfizer Inc.

  公开号：US20160251389A1

  公开（公告）日：2016-09-01

  The present invention relates to intermediates of Formula I and to methods of synthesizing and purifying calicheamicin derivatives.
• US9381205B2
  申请人：——

  公开号：US9381205B2

  公开（公告）日：2016-07-05
• US9872922B2
  申请人：——

  公开号：US9872922B2

  公开（公告）日：2018-01-23
• US9902691B2
  申请人：——

  公开号：US9902691B2

  公开（公告）日：2018-02-27