SP 1 | 26685-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: SP 1
• 英文别名: 8-(1,2-dimethyl-heptyl)-5,5-dimethyl-2-prop-2-ynyl-1,3,4,5-tetrahydro-2H-chromeno[4,3-c]pyridin-10-ol；SP 1 (pharmaceutical)；5,5-dimethyl-8-(3-methyloctan-2-yl)-2-prop-2-ynyl-3,4-dihydro-1H-chromeno[4,3-c]pyridin-10-ol
• CAS: 26685-57-4
• 化学式: C₂₆H₃₇NO₂
• 分子量: 395.585
• InChiKey: PNEYWTKVWJBOMD-UHFFFAOYSA-N

物化性质

• 沸点：
  517.8±50.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  SP 1 在 palladium on activated charcoal 作用下， 以 xylene 为溶剂， 反应 24.0h， 生成 8-(1,2-dimethyl-heptyl)-5,5-dimethyl-5H-chromeno[4,3-c]pyridin-10-ol
  参考文献：
  名称：

  大麻素。8-取代的10-羟基-5,5-二甲基-5H- [1]苯并吡喃并[4,3-c]吡啶及其衍生物的合成和中枢神经系统活性。

  摘要：

  DOI：

  10.1021/jm00221a031
• 作为产物：
  描述：

  2-benzyl-5,5-dimethyl-8-(1,2-dimethylheptyl)-10-hydroxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[4,3-c]pyridine 在 palladium on activated charcoal 氢气 、 sodium carbonate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 SP 1
  参考文献：
  名称：

  Drugs derived from cannabinoids. 1. Nitrogen analogs, benzopyranopyridines and benzopyranopyrroles

  摘要：

  Various nitrogen analogs of delta6a,10a-tetrahydrocannabinol were synthesized by a general procedure described in an earlier communication. Minimum effective doses (MED50's) and lethal doses (LD50's) were determined by a modified Irwin mouse screen after iv administration of compounds in PEG 200. The most potent compounds were the propargyl (5t), allyl (5m), and chloroallyl (5o-q) derivatives. Overt behavioral effects (CNS depression, static ataxia, and hypersensitivity) of 5t and Roger Adams' carbocyclic analog (III) were found to be similar in the mouse, cat, dog, and monkey. Dichloroisoproterenol prevented and reversed many of the depressant effects of both III and 5t but had no effect on the ataxia produced by these compounds. In antinociceptive tests, 5t was active in the phenylquinone and Eddy hot-plate tests but was inactive in the tail-flick test.

  DOI：

  10.1021/jm00226a001

文献信息

• Drugs derived from cannabinoids. 2. Basic esters of nitrogen and carbocyclic analogs
  作者：Raj K. Razdan、B. Zitko Terris、Harry G. Pars、Nicholas P. Plotnikoff、Patrick W. Dodge、Anthony T. Dren、Jaroslav Kyncl、Peter Somani

  DOI：10.1021/jm00226a002

  日期：1976.4

  Various basic esters of nitrogen (2) and carbocyclic (3 and 4) analogs of cannabinoids were synthesized using dicyclohexylcarbodiimide in methylene chloride. The compounds in the three series werw studied in selected pharmacological tests in mice, rats, dogs, and cats. It was shown that making the basic ester from the phenol retains biological activity and can lead to a greater selectivity of action

  使用二环己基碳二亚胺在二氯甲烷中合成了大麻素的氮的各种碱性酯（2）和碳环的碳酸酯（3和4）类似物。这三个系列化合物中的化合物已在小鼠，大鼠，狗和猫的选定药理试验中进行了研究。结果表明，由酚制备碱性酯保留了生物活性，并且可以导致更大的作用选择性，特别是抗伤害感受活性。氮类似物系列中最有趣的酯是5、6、10和14，碳环系列中的酯是19和20。在扭体，热板和甩尾试验中，化合物5比可待因更有效，目前正在临床试验中。化合物20在小鼠音频性癫痫发作测试中非常有效，并且作为抗血管生成剂很受关注。
• Heterocyclic esters of benzopyranopyridines
  申请人：Sharps Associates

  公开号：US03991194A1

  公开（公告）日：1976-11-09

  Novel heterocyclic esters of benzopyranopyridines represented by the formula ##SPC1## Wherein R.sub.1 is hydrogen, lower alkyl, lower alkanoyl, cycloalkyl-lower alkyl, cycloalkyl-lower alkanoyl, lower alkenyl, lower alkynyl, halo-loweralkenyl, phenyl-lower alkyl, phenyl-lower alkenyl or phenyl-lower alkynyl; R.sub.2 is lower alkyl; R.sub.3 is an alkyl having one to twenty carbon atoms or a cycloalkyl-lower alkyl, Y is a straight or branched chain alkylene having one to eight carbon atoms, and R.sub.4 is a group of the formula ##EQU1## a is an integer from 1 to 4, b is an integer from 1 to 4 and X is CH.sub.2, O, S or N--R.sub.5 with R.sub.5 being hydrogen or lower alkyl, with the limitation that when X is O, S or N--R.sub.5, a and b each must be 2 and R.sub.6 is hydrogen or a lower alkyl group bonded to a carbon in the ring; and the acid addition salts thereof.

  以下是苯并吡啶酮类新颖杂环酯的化学式：##SPC1## 其中，R.sub.1是氢、低碳基、低脂肪酰基、环烷基-低碳基、环烷基-低脂肪酰基、低烯基、低炔基、卤代低烯基、苯基-低碳基、苯基-低烯基或苯基-低炔基；R.sub.2是低碳基；R.sub.3是具有一到二十个碳原子的烷基或环烷基-低碳基；Y是具有一到八个碳原子的直链或支链烷基；R.sub.4是一个式子为##EQU1## 的基团；a是1到4的整数，b是1到4的整数，X是CH.sub.2、O、S或N-R.sub.5，其中R.sub.5是氢或低碳基，但当X为O、S或N-R.sub.5时，a和b必须各为2，R.sub.6是与环中碳原子相连的氢或低碳基；以及其酸加成盐。
• Anesthesia methods using benzopyrans and esters thereof as
  申请人：Abbott Laboratories

  公开号：US04025630A1

  公开（公告）日：1977-05-24

  Improved anesthesia methods comprising pretreating a patient to be anesthetized with a benzopyran of formula I ##STR1## wherein, in the C ring, X is NR.sub.1, S, CH.sub.2 or ##STR2## R.sub.1 is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, loweralkanoyl, cycloalkyloweralkyl, cycloalkylloweralkanoyl, cycloalkyl, haloloweralkyl, haloloweralkenyl, phenylloweralkyl, phenyloweralkenyl or phenyloweralkylnyl; m is an integer from 0 to 3, n is an integer from 0 to 3 and n + m = 2 or 3; or the C ring is quinuclidine ring ##STR3## R.sub.2 is loweralkyl; R.sub.3 is hydrogen or ##STR4## wherein Y is a straight or branched chain alkylene group having from one to eight carbon atoms, a is an integer from 1 to 4, b is an integer from 1 to 4, Z is CH.sub.2, O, S or NR.sub.6, R.sub.6 being hydrogen or loweralkyl, with the limitation that when Z is O, S or NR.sub.5, the sum of a and b is 3 or 4, and R.sub.5 is hydrogen or loweralkyl; R.sub.4 is C.sub.1 -C.sub.20 straight or branched chain alkyl, cycloalkyl, or ##STR5## wherein Y is a straight or branched chain alkylene group having from one to ten carbon atoms, and each R.sub.7, R.sub.8 and R.sub.9 are the same or different members of the group consisting of hydrogen, halo, trifluoromethyl or loweralkyl; and the pharmaceutically acceptable salts thereof, with the limitation that when X is ##STR6## m = 2 and n = 2, R.sub.3 cannot be hydrogen.

  改进的麻醉方法包括使用式I的苯并吡喃预处理待麻醉的患者，其中在C环中，X为NR.sub.1，S，CH.sub.2或##STR2##，R.sub.1为氢，低烷基，低烯基，低炔基，低酰基，环烷基低烷基，环烷基低酰基，环烷基，卤代低烷基，卤代低烯基，苯基低烷基，苯基低烯基或苯基低烷基基；m为0至3的整数，n为0至3的整数，n + m = 2或3；或C环为喹啉环##STR3##，R.sub.2为低烷基；R.sub.3为氢或##STR4##，其中Y为直链或支链烷基链，具有1至8个碳原子，a为1至4的整数，b为1至4的整数，Z为CH.sub.2，O，S或NR.sub.6，其中R.sub.6为氢或低烷基，限制条件为当Z为O，S或NR.sub.5时，a和b的和为3或4，R.sub.5为氢或低烷基；R.sub.4为C.sub.1-C.sub.20直链或支链烷基，环烷基，或##STR5##，其中Y为具有1至10个碳原子的直链或支链烷基链，每个R.sub.7，R.sub.8和R.sub.9是相同或不同的羟基，卤素，三氟甲基或低烷基成员的群；及其药学上可接受的盐，限制条件为当X为##STR6##时，m = 2且n = 2时，R.sub.3不能为氢。
• Novel heterocyclic esters of benzopyranopyridines
  申请人：Sharps Associates

  公开号：US04042694A1

  公开（公告）日：1977-08-16

  Novel heterocyclic esters of benzopyranopyridines represented by the formula ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, lower alkanoyl, cycloalkyl-lower alkyl, cycloalkyl-lower alkanoyl, lower alkenyl, lower alkynyl, halo-loweralkenyl, phenyl-lower alkyl, phenyl-lower alkenyl or phenyl-lower alkynyl; R.sub.2 is lower alkyl; R.sub.3 is an alkyl having one to twenty carbon atoms or a cycloalkyl-lower alkyl, Y is a straight or branched chain alkylene having one to eight carbon atoms, and R.sub.4 is a group of the formula ##STR2## a is an integer from 1 to 4, b is an integer from 1 to 4 and X is CH.sub.2, O, S or N--R.sub.5 with R.sub.5 being hydrogen or lower alkyl, with the limitation that when X is O, S or N--R.sub.5, a and b each must be 2 and R.sub.6 is hydrogen or a lower alkyl group bonded to a carbon in the ring; and the acid addition salts thereof.

  这是一种新型杂环酯化合物，其化学式为##STR1##其中，R.sub.1为氢、低碳基、低脂肪酰基、环烷基-低碳基、环烷基-低脂肪酰基、低烯基、低炔基、卤代低烯基、苯基-低碳基、苯基-低烯基或苯基-低炔基；R.sub.2为低碳基；R.sub.3为一种具有1到20个碳原子的烷基或环烷基-低碳基；Y为一种具有1到8个碳原子的直链或支链烷基；R.sub.4为##STR2##其中，a为1到4的整数，b为1到4的整数，X为CH.sub.2、O、S或N--R.sub.5，R.sub.5为氢或低碳基；需要注意的是，当X为O、S或N--R.sub.5时，a和b必须分别为2，且R.sub.6为与环中碳原子相连的氢或低碳基；此外，还包括其酸加成盐。
• Buchwald; Browne; Wu, Pharmazie, 2000, vol. 55, # 3, p. 196 - 201
  作者：Buchwald、Browne、Wu、Ji、Bodor

  DOI：——

  日期：——